Dictionary of Organometallic Compounds: First Supplement

Dictionary of
The Dictionary of Organometallic Compounds in three volumes published 1984
This First Supplement published 1985
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Library of Congress Cataloging in Publication Data British Library Cataloguing in Publication Data
Main entry under title:
1. Organometallic compounds-Dictionaries. 00411.053 1984 Suppl. 547'.05'0321 85-14994
ISBN 978-1-4615-6846-9
ISBN 978-1-4615-6846-9
DOI 10.1007/978-1-4615-6844-5
EXECUTIVE EDITOR
J.E. Macintyre
E.W. Abel
INTERNATIONAL ADVISORY BOARD
R.B. King University of Exeter B.l. Aylett* Queen Mary College, London M.A. Bennett Australian National University, Canberra
C. Floriani Universita di Pisa
W.A.G. Graham University of Alberta
D.l. Cardin Trinity College, Dublin
S.A. Cotton Stanground School, Peterborough
R.l. Cross University of Glasgow M. Green University of Bristol
P. G. Harrison University of Nottingham
University of Georgia
M. Kumada University of Kyoto M.F. Lappert* University of Sussex
1.F. Normant Universite Pierre et Marie Curie, Paris P.L. Pauson* University of Strathclyde
* Executive Members
SPECIAL EDITORS
R. Lalanandham Massachusetts Institute of Technology
1.B. Leach Oxford Polytechnic
1.D. Smith University of Sussex
K. Smith University College of Swansea
CONTRIBUTORS
D. Seyferth Massachusetts Institute of Technology
F.G.A. Stone University of Bristol
B.M. Trost University of Wisconsin
G. Wilke Max-Planck-Institut fur Kohlenforschung, Mulheim
A. C. Sullivan University of Sussex
B.l. Wakefield University of Salford
D.R.M. Walton University of Sussex
1.L. Wardell University of Aberdeen
C. White University of Sheffield
L.E. Smith, K. Hatton, R.l. Mercer, L. Mills, K.R. Nagl, C. Reeve, D.R. Saunders, T.L. Waring
vii
Introduction
For detailed information about how to use the Dictionary see the Introduction in Volume 1 of the Main Work.
1. Using the Supplement
As in the Main Work volumes, every Entry is numbered to assist ready location. The Entry Number consists of a metal element symbol followed by a five-digit number. In this first Supplement the first digit is invariably 1. Cross-references within the text to Entries having numbers beginning with zero refer to Main Work Entries.
Where a Supplement Entry contains additional or corrected information referring to an Entry in the Main Work, the whole Entry is reprinted, with the accompanying statement "Updated Entry replac ing ... ". In such cases, the new Entry contains all of the information which appeared in the correspond ing Main Work Entry, except for any which has been deliberately deleted. There should therefore be no necessity for the reader to consult the Main Work.
Chemical Names Names reported in Chemical Abstracts since 1981 are labelled with the suffix 11CI. It is possible however that some further changes may take place before the publication of the 11 th Collective Index covering the period 1982-86.
2. Literature Coverage
In compiling this Supplement the primary literature has been surveyed to mid 1984 and a considerable amount of information from later literature has also been included. In accordance with our policy of continually enhancing the usefulness of the Diction ary, a number of other compounds have been added for the first time. Some of these were suggested by users, to whom we are grateful.
3. Sources of Further Information
The following selected references to recent books and review articles provide more information about various aspects of organometallic chemistry. To gether with references given in the Introduction to the Main Work, they cover the literature up to mid 1984.
IX
General
Jolly, P.W. et ai, Adv.Organomet.Chem., 1981, 19, 257 (the application of C-13 nmr spectroscopy to organo-transition metal complexes)
Davies, S. G., Organotransition-metal Chemistry: Applications to Organic Synthesis, Pergamon Press, Oxford, 1982.
Bruce, M.I., J.Organomet.Chem., 1983, 257, 417 (complexes containing heteronuclear M-M bonds: recent advances 1980-1981, heterometallic cluster complexes)
Hegedus, L.S., Modern Synthetic Methods, 1983,3, 61 (group Vill transition metals in organic synthesis)
Homogeneous Catalysis with Metal Phosphine Complexes, Pignolet, L.H. Ed., Plenum, N.Y., 1983.
Rockett, B.W. etal,J.Organomet.Chem., 1983,242, 1; 257, 275 (organic reactions of selected complexes: annual survey covering the years 1981 and 1982)
Schmidbaur, H., Angew.Chem.Int.Ed.Engl., 1983, 22, 907 (Phosphorus ylides in the coordination sphere of transition metals: an inventory)
Stille, J.K., Modern Synthetic Methods, 1983, 3, 1 (principles of transition metals in organic synthesis)
Werner, H., Angew.Chem.Int.Ed.Engl., 1983, 22, 927 (electron-rich half-sandwich complexes par excellence)
Colquhoun, H.M. et ai, New Pathways for Organic Synthesis: Practical Applications of Transition Metals, Plenum Press, N.Y., 1984.
Dotz, K.H., Angew.Chem.Int.Ed.Engl., 1984, 23, 587 (carbene complexes in organic synthesis)
Heaton, B.T., J.Organomet.Chem., 1984, 12, 143 (organometallic compounds containing M-M bonds)
Hegedus, L.S., J.Organomet.Chem., 1984,261,283; 1985,283, 1 (transition metals in organic synthesis: annual surveys covering the years 1982 and 1983)
Mann, B.E., Spectroscopic Properties of Inorganic and Organometallic compounds, 1984, 16, 1 (review of nmr covering the literature up to late 1982)
Marko, L., J.Organomet.Chem., 1984, 261, 485; 1985, 283, 221 (transition metals in organic synthesis: hydroformylation, reduction and oxi dation: annual surveys covering the years 1982 and 1983)
First Supplement
Stone, F.G.A., Angew. Chem.lnt. Ed. Engl. , 1984, 23,89 (M-C and M-M multiple bonds as ligands in transition metal chemistry: the isolobal connection)
Ernst, R.D., Accs.Chem.Res., 1985, 18, 56 (metal pentadienyl chemistry)
The Chemistry of the Carbon-Metal Bond, Hartley, F.R. and Patai, S.Eds, Wiley-Interscience, N.Y., 1985,2.
Pearson, A.J., Metallo-Organic Chemistry, Wiley, 1985.
AI Aluminum
Smith, J.D., J.Organomet.Chem., 1982, 227, 241; 1983,257, 17 (aluminum: annual surveys covering the years 1980 and 1981)
Voronkov, M. et ai, J.Organomet.Chem., 1982,239, 199 (alumatranes)
Davidson, G., Coord.Chem.Rev., 1983, 49, 117 (elements of group /11)
Marina, N.G., et ai, Russ.Chem.Rev., 1983,52,413 (relation between the nature of the components of titanium-containing Ziegler systems and their act ivity and stereospecificity in the polymerisation of dienes)
Barbot, F., Bull. Soc. Chim.Fr. , 1984,83 (synthesis and reactivity of organoaluminum compounds derived from unsaturated halides)
As Arsenic
Zingaro, R.A. et ai, J. Organomet. Chem., 1983,257, 67 (arsenic: annual surveys covering the years 1980 and 1981)
Au Gold
Anderson, G.K., Adv.Organomet.Chem., 1982,20, 40 (the organic chemistry of gold)
BBoron
Peiter, A. and Smith, K., Comprehensive Organic Chemistry, Barton, D.H.R. et al Eds, Pergamon, Oxford, 1979,3,389.
Davidson, G., Coord. Chem.Rev. , 1983, 49, 117 (elements of group III)
Kabalka, G.W., J.Organomet.Chem., 1984, 274, 1 (boranes in organic synthesis: annual survey covering the year 1982)
Mikhailov, B.M. and Bubnov, Yu., Organoboron Compounds in Organic Synthesis, Harwood Acad emic Publishers, London, 1984.
Niedenzu, K., J.Organomet.Chem., 1984, 261, 1 (boron: annual survey covering the year 1982)
x
BiBismuth
Doak, G.O. et ai, J.Organomet.Chem., 1984, 261, 59 (bismuth: annual survey covering the year 1982)
Co Cobalt
Scheffold, R. et ai, Modern Synthetic Methods, 1983, 3, 355 (vitamin B 12 and related cobalt complexes as catalysts in organic synthesis)
Bonnemann, H. et ai, Aspects Homogeneous Catal., 1984, 5, 75 (cobalt-catalysed synthesis of pyridine and its derivatives)
Mague, J.T., J.Organomet.Chem, 1984, 261, 103 (cobalt, rhodium and iridium: annual survey covering the year 1982)
Marko, L., Fundam.Res.Homogeneous Catal., 1984, 4, 1 (review covering the mechanisms of hydroformylation reactions catalysed by unsubsti tuted cobalt carbonyls)
Toscano, P.J. et ai, Progr.lnorg.Chem., 1984, 31, 105 (B 12 and related organocobalt chemistry: formation and cleavage of cobalt-carbon bonds)
Vollhardt, K.P.C., Angew.Chem.lnt.Ed.Engl., 1984, 23, 539 (cobalt mediated [2+2+2] cycloadditions: a maturing synthetic strategy)
Cr Chromium, Mo Molybdenum and W Tungsten
Atwood, J.D., J.Organomet.Chem., 1983,257, 105 (chromium, molybdenum and tungsten: annual survey covering the year 198I)
CuCopper
Posner, G.H., An Introduction to Synthesis Using Organocopper Reagents, Wiley, 1980.
Erdik, E., Tetrahedron, 1984, 40, 641 (copper catalysed reactions of organolithiums and Grig nard reagents)
Fe Iron
Kerber, R.C., J.Organomet.Chem., 1984,278,205 (organoiron chemistry: annual survey covering the year 1983)
Rockett, B.W. etal, J.Organomet.Chem., 1984,278, 255 (jerrocene: annual survey covering the year 1983)
Ga Gallium and In Indium
Tanaka, T., J. Organomet. Chem., 1982, 227, 289 (gallium and indium: annual survey covering 1980)
Davidson, G., Coord. Chem.Rev. , 1983, 49, 117 (elements of group Ill)
Ge Germanium
Molloy, K.c. et ai, Adv.lnorg.Chem.Radiochem., 1983, 27, 113 (structural organogermanium chem istry)
Armitage, D.A., Organometallic Compounds, 1985, 13, 1 (silicon, germanium, tin and lead)
HfHafnium
Fay, R.C., Coord. Chem.Rev. , 1982, 45, 41 (zirco nium and hafnium)
Cardin, D.J., Lappert, M.F. and Raston, c.L., Organometallic Chemistry of Zirconium and Hafnium, Horwood-Wiley, Chichester, 1985.
HgMercury
Ir Iridium
Mague, J.T., J.Organomet.Chem., 1984, 261, 103 (cobalt, rhodium and iridium: annual survey covering the year 1982)
Janowicz, A.H. etal, Pure Appl.Chem., 1984,56,13 (oxidative addition of soluble iridium and rhodium complexes to carbon-hydrogen bonds in methane and higher alkanes)
La Lanthanides
Schumann, H., Angew.Chem.lnt.Ed.Engl., 1984, 23,474 (organolanthanoid complexes)
LiLithium
Miginiac, L., J. Organomet. Chem., 1982, 238, 235 (the synthetic possibilities of addition reactions between common organometallic compounds and conjugated enynes)
Xl
Kaiser, E.M., Tetrahedron 1983, 39, 2055 (lateral metallation of methylated nitrogenous hetero cycles)
Marsais, F. et ai, Tetrahedron 1983, 39, 2009 (metallation of rr-deficient heteroaromatic compounds)
Narasimhan, N.S., et ai, Synthesis, 1983, 957 (syntheses of heterocyclic compounds involving aromatic lithiation reactions in the key step)
Vara Prasad, J.Y.N., et ai, J.Organomet.Chem., 1983, 259, 1 (carbometallation: addition of organo metallic compounds to isolated multiple bonds in functionally substituted compounds)
Werstiuk, N.T., Tetrahedron, 1983,39,206 (homo enolate anions and homoenolate anion equivalents)
Whitesell, J.K., et ai, Synthesis, 1983, 517 (alky lation of ketones and aldehydes via their nitrogen derivatives)
Arseniyadis, S., et ai, Org.React., 1984, 31, 1 (addition and substitution reactions of nitrile stabilised carbanions)
Beak, P., et ai, Chem.Rev., 1984, 84, 471 (metal lation and electrophilic substitution of amine derivatives adjacent to nitrogen: oc-metallo amine synthetic equivalents)
Erdik, E., Tetrahedron, 1984, 40, 641 (copper(I) catalysed reactions of organolithiums and Grig nard reagents)
Schleyer, P.Y.R., Pure Appl.Chem., 1984, 56, 151 (remarkable structures of lithium compounds)
Seyferth, D., etal, 1sr.J.Chem., 1984,24,167 (direct nucleophilic acylation with acyllithium reagents: acyl anion synthons unmasked)
Mg Magnesium
Dagonneau, M., Bull. Soc. Chim.Fr. , 1982, 269 (radical reactions of organomagnesiums)
Miginiac, L., J.Organomet.Chem., 1982, 238, 235 (the synthetic possibilities of addition reactions between common organometallic compounds and conjugated enynes)
Holm, T., Acta Chem.Scand.B, 1983, 37, 567 (electron transfer from alkylmagnesium com pounds to organic substrates)
Vara Prasad, J.Y.N., et al, J.Organomet.Chem., 1983,259, 1 (carbometallation: addition of organo metallic compounds to isolated multiple bonds in functionally substituted compounds)
Bartoli, G., Accs.Chem.Res., 1984, 17, 109 (conju gate addition of alkyl-Grignard reagents to mono nitroarenes)
Erdik, E., Tetrahedron, 1984, 40, 641 (copper(I) catalysed reactions of organolithiums and Grig nard reagents)
First Supplement
Treichel, P.M., J.Organomet.Chem., 1984,261, 31 (manganese, technetium and rhenium: annual survey covering the year 1982)
Os Osmium and Ru Ruthenium
Adams, R.J., et ai, Accs.Chem.Res., 1983, 16, 67 (chemistry of triosmium carbonyl cluster compounds and its implications for catalysis)
Bradley, J.S., Adv.Organomet.Chem., 1983, 22, 1 (the chemistry of carbidocarbonyl clusters)
Johnson, B.F.G., et ai, J.Organomet.Chem., 1983, 249, 255 (metal-carbido complexes of ruthenium and osmium)
Keister, J.B., J.Organomet.Chem., 1983, 245, 409; 1984, 274, 457 (ruthenium and osmium: annual surveys for the years 1981 and 1982)
Seddon, E.A. and Seddon, K.R., The Chemistry of Ruthenium, Elsevier, 1984.
PbLead
Wolters, J., et ai, J.Organomet.Chem., 1984, 274, 211 (lead: annual survey covering the year 1982)
RhRhodium
Knowles, W.S., Accs.Chem.Res., 1983, 16, 106 (asymmetric hydrogenation)
Drury, D.J., Aspects Homogeneous Catal., 1984,5, 197 (homogeneous catalysis using iodide promoted rhodium catalysts)
Janowicz, A.H., et ai, Pure Appl.Chem., 1984,56, 13 (oxidative addition of soluble iridium and rhodium complexes to carbon-hydrogen bonds in methane and higher alkanes)
Mague, J.T., J.Organomet.Chem., 1984, 261, 103 (cobalt, rhodium and iridium: annual survey covering the year 1982)
Sb Antimony
Freedman, L.D., et ai, J.Organomet.Chem., 1984, 261,31 (antimony: annual survey covering the year 1982)
Si Silicon
Weidenbruch, M., et aI, Rev. Silicon, Germanium, Tin, Lead Compds., 1983,7, 127 (steric effects in organosilicon chemistry)
XII
Williams, E.A., Ann.Reports NMR Spectrosc., 1983, 14, 235 (recent advances in silicon-29 nmr spectroscopy)
Ager, D.J., Synthesis, 1984, 384 (the Peterson reaction)
Chernyshev, E.A., et ai, J.Organomet.Chem., 1984, 271,129 (gas phase reactions of dichlorosilylene)
Corriu, R.J.P. et ai, Selectivity - a Goal for Synthetic Efficiency, Bartman, W. and Trost, B.Eds, Work shop Conferences Hoechst, Verlag Chemie, 1984, 14,21.
Corriu, R.J.P., et ai, Topics Stereochem., 1984, 15, 43 (stereochemistry at silicon)
Cragg, R.H., et ai, J. Organomet. Chem., 1984,267, 1 (organo-1 ,3, 2-dioxasilaheterocycles)
Egorochkin, A.N., Russ. Chem.Revs. , 1984,53,445 (the spectroscopy of organic compounds of silicon sub-group elements and hyperconjugation)
Gladyz, J.A., Accs.Chem.Res., 1984, 17, 326 (new synthetic chemistry of transition metal trialkylsilane complexes)
Larson, G.L., J.Organomet.Chem., 1984, 274, 29 (the Si-C bond: annual survey covering the year 1982)
Parnes, Z.N., et ai, Synthesis, 1984, 991 (reactions proceeding with cleavage of silicon-carbon bonds in tetraorganosilanes and formation of new carbon carbon bonds under the action of Lewis acids: applications to organic synthesis)
Razuvaev, G.A., et ai, J.Organomet.Chem., 1984, 271, 261 (reactions of organopolysilanes with organo peroxides)
Stowell, J.e., Chem.Revs., 1984, 84, 409 (three carbon homologating agents)
Vollhardt, K.P.e., Angew.Chem.lnt.Ed.Engl., 1984, 23, 539 (cobalt-mediated [2+ 2+ 2] cycloadditions: a maturing synthetic strategy)
SnTin
Smith, P.J., J.Organomet.Chem.Library, 1981, 12, 98.
Cusak, P.A., et ai, A Bibliography of X-Ray Crystal Structures of Tin Compounds, International Tin Research Institute Publication No. 588.
Ti Titanium
Pez, G.P., et ai, Adv.Organomet.Chem., 1981, 19, 51 (chemistry oftitanocene and zirconocene)
Fay, R.C., Coord.Chem.Rev., 1982,45,1 (titanium)
Reetz, M.T., Top. Curr. Chem., 1982, 106, 1 (organotitanium reagents in organosynthesis: a simple means to adjust reactivity and selectivity of carbanions)
Toogood, G.E., et ai, Adv.Inorg.Chem.Radio chem., 1982, 25, 267 (hydride compounds of the titanium and vanadium group elements)
Marina, N.G., et ai, Russ.Chem.Rev., 1983,52,413 (relation between the nature of the components of titanium-containing Ziegler systems and their acti vity and stereospecificity in the polymerisation of dienes)
Seebach, D., et ai, Pure Appl. Chem., 1983, 55, 1807 (recent advances in the use of titanium reagents in organic synthesis)
Weidmann, B., et ai, Angew.Chem.Int.Ed.Engl., 1983, 22, 31 (organometallic compounds of titanium and zirconium as selective nucleophilic reagents in organic synthesis)
TI Thallium
Davidson, G., Coord.Chem.Rev., 1983, 49, 117 (elements of group Ill)
xiii
First Supplement
Hiu, B.C., Kirk-Othmer Encycl. Chem. Technol., 3rd Edn, Grayson, M., et al Eds, Wiley, N.Y., 1983, 22,885 (thallium and thallium compounds)
Zr Zirconium
Negishi, E., Pure Appl.Chem., 1981, 53, 2333 (zirconium in organic synthesis)
Pez, G.P., et ai, Adv.Organomet.Chem., 1981, 19, 51 (chemistry of titanocene and zirconocene)
Schwartz, J., et ai, Organic Synthesis Today and Tomorrow, Trost, B.M. and Hutchinson, C.R. Eds, Pergamon, Oxford, 1981 (zirconium reagents in organic synthesis)
Fay, R.C., Coord. Chem.Rev. , 1982, 45, 41 (zirco nium and hafnium)
Seebach, D., Modern Synthetic Methods, 1983, 3, 317 (titanium and zirconium derivatives in organic synthesis)
Weidmann, B. et ai, Angew. Chem. Int. Ed. Engl. , 1983, 22, 31 (organometallic compounds of tita nium and zirconium as selective nucleophilic reagents in organic synthesis)
Cardin, D.J., Lappert, M.F. and Raston, c.L., Organometallic Chemistry of Zirconium and Hafnium, Horwood-Wiley, Chichester, 1985.
Contents First Supplement Entries
xv
Ris( cyclohexyl isocyanide )silver( 1 +)
M 326.209 (ion)
Isocyanide ligands replaced by phosphines, bipy. Perchlorate: [86550-06-3].
Cl4HzzAgCINz04 M 425.660 Translucent waxy eryst. Sol. EtOH, CHCI3. Ir VN~ 2215,2190 em-I; raman VN~ 2232 em-I.
Bell, A. et ai, J. Chern. Soc., Dalton Trans., 1984, 1317 (synth, props, ir, raman, nmr, cmr)
C2oHy;AgN4$ Ag-10002 Tetrakis(2-isocyano-2-methylpropane )silver( 1 +), Ila
Tetrakis(tert-butyl isocyanide)silver(J +). Tetrakis(J,l dimethylethyl isocyanide)silver(J +)
M 440.399 (ion) Perchlorate: [86631-61-0]. Colourless eryst. Sol. CHCI3,
EtOH. Ir VN~ 2188, 2172 em-I; raman VN~ 2193, 2180 em-I.
Bell, A. et ai, J. Chern. Soc., Dalton Trans., 1984, 1317 (synth, props, ir, raman, nmr, cmr)
C24H4~g2N2Si4 Ag-10003 Bis[l'-{ 2-pyridinylbis( trimethy Isily I)methy 1-C: N]disilver, II Cl
[92889-58-2]
M 688.703 Colourless eryst. Sol. pentane, THF. Light-sensitive. Sta
ble at r.t. for days. Papasergio, R.I. et ai, J. Chern. Soc., Chern. Commun., 1984,
612 (synth, struct)
Ris[J ,3-bis(J ,l-dimethylethyl)-2-isocyano-5- methylbenzene]silver(1 +)
F F \ /
H3CVC(CH3h (H3C)3C~CHJ hexajiuorophosphate
M 566.597 (ion) PF6-eounterion coordinated in solid state. HexaJluorophosphate:
C3zH46AgF6NzP M 711.561 White eryst. Sol. CHCI3, DMSO, C6H6, CH2Cb. Mp 205-207° dec. Ir VN=C 2199, 2170, 2122 em-I. 1: 1 electrolyte in soln.
Yamamoto, Y., lnorg. Chim. Acta, 1982,68,75 (synth, cryst struct, ir)
Al Aluminum CJll9A1 Trimetbylaluminum, 9CI
AI-10001
M 72.086 Dimeric at 70°.
R R R ).( \(
R/ "R/ "R
Dimer: Di-JL-methyltetramethyldialuminum. Hexamethyldialuminum. Methylating agent for tertiary alcohols, ketones, etc. Liq. d20 0.752. Mp 15.4°. Bp 130°, Bps 20°.
TMEDA complex (2:1): [30471-04-6]. Hexamethyl[JL (N ,N:N',N'-tetramethylethylenediamine)] dialuminum. C12H34AhN2 M 260.377 White solid. Mp 136-139°.
Me2N(CH2hNMe2 complex (2:/): [30471-06-8]. Hexa methyl[JL-(N,N :N',N'-tetramethyl-l ,3- propanediamine)] dialuminum. CI3H~12N2 M 274.404 White solid. Mp 166-169°.
Diglyme complex (2:1): [16103-63-2]. [JL- [Bis( 2- methoxyethyl)ether]] hexamethyldialuminum. (2,2' Dimethoxydiethyl ether)bis(trimethylaluminum). Mp 3-5°. Bpo.oOJ 83-85°.
N-Methylmorpholine complex (2:/): Hexamethyl[J.!-(4- methylmorpholine)]dialuminum. ClIH29AhNO M 245.319 Colourless cryst. Mp 67-69°. BP4 123-125°.
N-Methylmorpholine complex: [14878-33-2]. Tri methyl( 4-methylmorpholine )aluminum. CgH 2oAION M 173.234 Needles or plates (hexane). Mp 50-51 0.
N,N'-Dimethylpiperazine complex (2:1): [14878-34-3]. [J.!-( I ,4 -Dimethylpiperazine)] hexamet hyldialuminum. C12H32AhN2 M 258.361 Cryst. (hexane). Mp 200-201 0. BP3 140-145°.
N,N'-Dimethylpiperazine complex: [14878-35-4]. (J ,4- Dimet hylpiperazine )trimethylaluminum. C9H23AIN2 M 186.276 Cryst. (hexane). Mp 62-63°.
Formaldehyde complex: [82495-17-8]. C4H IIAIO M 102.112 Reacts with alkenes to give allylic alcohols and with enol ethers to give threo-I ,3-diols. Formed and used in situ in CH 2Ch (heptane).
4-Methylpyridine complex: [88008-81-5]. Trimethyl( 4- methylpyridine )aluminum. C9HJ6A1N M 165.214 White solid. So!. C6H 6. Mp 74.5-75.8°.
2
Me3CCN complex: (2,2-Dimethylpropanenitrile) trimethylaluminum. (tert-Butyl cyanide) trimethylaluminum. CSHlsAlN M 155.218 Colourless cryst. So!. C6H 6. Mp 61 0. BPo.oJ 55-60° sub!. Dec. on heating to Dimethyl [(1,2,2- trimethylpropylidene)amino]aluminum, AI-10016 .
Hexamethyltetramine complex (1:2): see Hexamethyl[J.!-(J ,3,5,7 -tetraazatricyc!o[3.3.1.13,7] decane-NI:N3)]dialuminum, AI-lO042
Hexamethylenetetramine complex (1:1): see Trimethyl(I,3,5,7-tetraazatricyc!o[3.3.1.1 3,7]decane N/)aluminum, AI-lO026
Bamford, C.H. et ai, J. Chern. Soc., 1946,468 (synth) Ziegler, K. et ai, Justus Liebigs Ann. Chern., 1954,589, 91
(synth) Jennings, J.R. et ai, J. Chern. Soc., 1965,5083 (derivs, synth, ir,
prnr) Ramey, K.C. et ai, J. Phys. Chern., 1965,69,3418 (pmr) Thiele, K.-H. et ai, Z. Anorg. AI/g. Chern., 1966, 348, 179. Williams, K.C. et ai, J. Am. Chern. Soc., 1966,88,5460 (prnr) Lehmkuhl, H. et ai, Justus Liebigs Ann. Chern., 1967,705,23
(deriv) Ogawa, T., Spectrochirn. Acta, Part A, 1968, 24, 15 (ir, raman) Chambers, D.B. et ai, J. Chern. Soc. (A), 1969, 1712 (rns) Jeffery, E.A. et ai, Aust. J. Chern., 1969,22, 1120 (prnr) Tanaka, J. et ai, Inorg. Chern., 1969,8,265 (rns) Pasynkiewicz, S. et ai, J. Organornet. Chern., 1970,25,29
(synth) Huffman, J.e. et ai, J. Chern. Soc., Chern. Cornrnun., 1971,911
(cryst struct) Yasuda, H. et ai, J. Organornet. Chern., 1973,49,103 (deriv,
synth, ir) Bochkarev, V.N. et ai, J. Gen. Chern. USSR, 1979,49,2019;
1981,51, 1045 (rns) Snider, B.B. et ai, J. Org. Chern., 1982,47, 3643; 1983,48, 2789
(use) Dorogy, W.E. et ai, Inorg. Chirn. Acta, 1983,73,31 (synth,
prnr, crnr, AI-27 nrnr, deriv) Shuler, R.L. et ai, Inorg. Chirn. Acta, 1984,85, 185 (deriv, nrnr) Fieser, M. et ai, Reagents for Organic Synthesis, Wiley, 1967-
84,8,506 (use) Bretherick, L., Handbook of Reactive Chemical Hazards, 2nd
Ed., Butterworths, London and Boston, 1979,449. Sax, N.I., Dangerous Properties of Industrial Materials, 5th
Ed., Van Nostrand-Reinhold, 1979,355. Hazards in the Chemical Laboratory, (Bretherick, L., Ed.), 3rd
Ed., Royal Society of Chemistry, London, 1981,521.
C3H 9AIN039
Trimethyl(nitrato-O)aluminate(l-), lOCI
C3H9AIKN03 M 173.189 Colourless, air-sensitive cryst. + I C6H6.
AI-10002
CJIuAIS - C6H15AI
Atwood, 1.L. et ai, J. Organomel. Chem., 1978,155, 1 (synlh, erysl slrucl)
Rogers, R.D. el ai, J. Cryslal/ogr. Spec. Res., 1984, 14, 1; CA, 100,16542 (erysl slrucl, deriv)
C4H IIAIS (Ethanethiolato)dimethylaluminum, 11CI
Molecular complexity not established. Catalyst for Beckmann rearrangements. Not isol., used in situ in hexane.
Maruoka, K. el ai, J. Am. Chem. Soc., 1983, 105, 2831 (synlh, use)
AI-10004 Dimethyl( N -methylmethanesulfinamidato )aluminum
Me 1
O ...... S..--N, 1 R
methanesulfinamidato-N:O)]dialuminum, lOCI.
CgH24AhN202S2 M 298.373 Colourless solid, air- and moisture-sensitive. Sol. CHCI3, CH2Cl2, C6H6, insol. pentane. Thought to exist as mixt. of conformational isomers.
Klerks, 1.M. el aI, J. Organomet. Chem., 1981,214, I (synlh, ir, nmr, cmr)
C4H12AIOPS AI-1000S (Dimethylphosphinothioato)dimethylaluminum,9C1 Updated Entry replacing AI-00091
Dimethylaluminum dimethylthiophosphinate [52110-44-8]
M 166.154 Oimeric.
Dimer: [54388-47-5]. Bis[J.I.-(dimethylphosphinothioato O:S)]tetramethyldialuminum,9C1. CgH24AI202P2S2 M 332.307 White cryst. (C6H6). Sol. C6H6, Et20, pentane. Mp 71-72°. Bpoooo) 45-50°.
Schaible, B. el aI, Z. Anorg. AI/g. Chern., 1974,403,289; 409, 176 (synth, pmr, nrnr, ir)
CSHI4AIP AI-10006 Dimethyl[(dimethylphosphino)methyl]aluminum
Me2AICH2PMe2
3
Karsch, H.H. el aI, Phosphorus Sulfur, 1983, 18,287 (synlh)
C6HI4AIN AI-10007 Dimethyl[ (l-methylpropyJidene )amino ]aluminum
[( sec-Butylidene )amino] dimethylaluminum. Dimethyl sec-butylideneaminoaluminum
M 127.165 Oimeric.
Me R , " Al Me /" R' )=N N=< R' "Al/ Me
I '- R Me
Dimer: Bis-J.l.-[(I -methylpropylidene)aminato] tetramethyldialuminum. C12H28AI2N2 M 254.330 Colourless cryst. Reacts with air and moisture. Mp 73°. Bpo.o) 60° sub!.
lennings, 1.R. el aI, J. Chem. Soc., 1965, 5083 (synlh, ir, pmr)
C6H14AIzNzSz AI-10008 [J.I.-[Ethanedithioamidato(2-)-N,S':N' ,S]]
tetramethyldialuminum, I1CI Bis(dimethylaluminum)dithiooxamide. Bis(dimethyla luminum) ethanedithioamidate [86356-15-2]
R = H
M 232.273 Yellow air-sensitive solid (toluene). Mp ca. 40° dec. Halder, T. el aI, J. Organomel. Chem., 1983,246,29 (synlh, ms,
prnr, ir, raman)
Aluminum triethyl. Triethylalane As Trimethylaluminum, AI-IOOOI with
R = Et
M 114.166
Oimeric. Colourless liq. Air- and moisture-sensitive. At 120° gives (MeCEt:NAIEt2h
t> Reacts violently with H 20 or alcohols. Pyrophoric. Highly toxic. B02050000.
Dimer: Hexaethyldialuminum. C12H30Ah M 228.332
Liq. d25 0.832. Mp -46° (-52.5°). Bp 194°, Bp13 100°.
Tetramethylhydrazine complex: CloH27AlN2 M 202.318 Colourless liq. BPo.4 78 0.
MeCN complex: [18307-84-1]. Colourless liq., air- and moisture-sensitive. Mp -6°. At 120° gives Di methyl[ (I-methylpropylidene )amino ]aluminum, Al- 10007.
Pajaro, G., Ann. Chim. (Rome), 1958,48,193 (synth) Hoffmann, E.G., Z. Elektrochem., 1960,64,616 (ir, raman) Ziegler, K. et ai, Justus Llebigs Ann. Chem., 1960,629, I
(synth) Jennings, J.R. et ai, J. Chem. Soc., 1965, 5083 (synth, ir, pmr,
deriv) Starowieyski, K. et ai, Roczniki Chem., 1966,40,47; CA, 65,
3704 (ir, deriv) Ramey, K. et ai, J. Phys. Chem., 1965,69,3418 (pmr) Nesmeyanov, A.N. et ai, The Organic Compounds of Boron,
Aluminum, Gallium, Indium and Thallium, 1967, North· Holland, Amsterday (rev)
Chambers, D.B. et ai, J. Chem. Soc. (A), 1969, 1712 (ms) Dewar, M.J.S. et ai, J. Chem. Soc., Dalton Trans., 1973,2381
(nqr) Kaminsky, W. et ai, Justus Liebigs Ann. Chem., 1975,438
(pmr) Rottler, R. et ai, Z. Naturforsch., B, 1976,31, 730 (cmr) Bochkarev, V.N. et ai, J. Gen. Chem. USSR, 1979,49,2019
(ms) Cocco, L. et ai, J. Org. Chem., 1979, 179, I (cmr) Bretherick, L., Handbook of Reactive Chemical Hazards, 2nd
Ed., Butterworths, London and Boston, 1979,606. Sax, N.I., Dangerous Properties of Industrial Materials, 5th
Ed., Van Nostrand-Reinhold, 1979, 1050.
C~17Alpe AI-10010 [(Dimethylphosphino )methyl]trimethylaluminate(l-)
[Al(CH2PMe2)Me3]e
M 147.156 (ion) Li salt, TMEDA complex: C12H3~ILiN1P M 270.302 Colourless air-sensitive cryst. + 1 THF. Sol. THF. In soln. slowly disproportionates to [Li(TME DA)][AlMe4] and [Li(TMEDA)][(PMe- 2CH2hAlMe2].
Karsch, H.H. et ai, J. Chem. Soc., Chem. Cammun., 1984, 1415 (synth)
C~lsAhCle AI-10011 #,-Chlorohexamethyldialuminate(l-), 1IC1
[Me3Al-CI-AlMe3]e
C38Hs4AI1ClK06 M 735.355 Colourless air- and moisture-sensitive solid + 2C6H6.
Atwood, J.L. et ai, J. Inarg. Nucl. Chem. Lett. Phenomena, 1983, 1, 199; CA, 101, 38516 (synth, cryst struct)
AI-10012 Chloromethy I[ (1,2,2-trimethylpropylidene )amino ]aluminum As Dimethyl [(l-methylpropylidene)amino]aluminum, AI-
10007 with
Jennings, J.R. et ai, J. Chem. Soc., 1965,5083 (synth, ir)
C7H lsAIN Diethyl(l-propanaminato )aluminum, lOCI
[77924-59-5]
AI-10013
Molecular complexity not reported. Reagent for aminoly sis of epoxides. Used in situ.
Overman, L.E. et ai, Tetrahedron Lett., 1981,22,195 (use)
CSHIOAICIO (2-Chlorophenolato)dimethylaluminum, lOCI
Dimethylaluminum 2-chlorophenoxide [64502-32-5]
Exists as mixt. of dimer and trimer. White air-sensitive solid.
Pasynkiewicz, S. et ai, J. Organamet. Chem., 1977, 132, 191 (synth, ir, pmr)
CSH 13A1N Dimethyl( 4-methylpyridine )aluminum
Dimethylaluminum ,),-picoline
C16H16AI1Nl M 300.358
AI-10015
Blue oil. Sol. cyclopentane. Diamagnetic. Soln. in pentane is brilliant red by reflected light and green by transmitted light.
Dorogy, W.E. et ai, [narg. Chim. Acta, 1983,72, 187; 73, 31 (synth, uv, pmr, cmr, A/-27 nmr)
CSHISAIN AI-10016 Dimethyl[ (1 ,2,2-trimethylpropylidene )amino ]aluminum As Dimethyl [( I-methylpropylidene )amino] aluminum, AI-
10007 with
tetramethyldialuminum. C16H~hN2 M 310.437 Colourless cryst. Mp 113°. Bpo.o! 110-120°.
Jennings, J.R. et ai, J. Chern. Soc., 1965,5083.
CSH 1sAhN2S 2 AI-10017 [1'-[ N,N' -Dimethylethanedithioamidato(2-)-N,S':N' ,S]]
tetramethyldialuminum, lICI Bis(dimethylaluminum) dithiodimethyloxamide [86356-16-3] As [J.I-[Ethanedithioamidato(2- )-N,S':N',Sll
tetramethyldialuminum, AI-l 0008 with
M 260.327 Colourless air-sensitive solid (toluene). Mp 90° dec.
BpO.OOOOO6 90° subl. Halder, T. et ai, J. Organornet. Chern., 1983, 246, 29 (synth, rns,
ir, rarnan, prnr)
[85004-93-9]
CSH22AIP29 AI-10019 Bis[ (dimethylphosphino )methyl]dimethylaluminate( 1-)
(Me2PCH2hAIMe29
CI4H38AlLiN2P2 M 330.338 Colourless cryst., air- and moisture-sensitive. Sol. THF. 3!P nmr 0 -50.8 ppm (reI. 85% H3P04).
Karsch, H.H. et aI, J. Chern. Soc., Chern. Cornrnun., 1984, 1415 (synth, cryst strucr)
CSH2~ISiz Hydrobis[(trimethylsilyl)methyl]aluminum,IICI
Bis(trimethylsilylmethyl)alane [85004-94-0]
AI-10020
Colourless cryst. (hexane). Sol. hydrocarbons. Mp 35- 36°. Bp 40-70° in vacuo subl.
Beachley, O.T. et aI, Organornetallics, 1983,2, 796 (synth, ir, prnr)
5
dimethylaluminum, lOCI [65293-62-1 ]
"/,,/ Me-P P-Me
~j I \
Me Me
Colourless air- and moisture-sensitive cryst. Sol. CH2Ch, THF, C6H6. Mp 73.5°. Bpo.! 115-120° subl. Dec. >200°.
Schmidbaur, H. et aI, Monatsh. Chern., 1980, 111, 1233 (synth, ir, rns, prnr, crnr, P-31 nrnr, Li-7 nrnr)
C9Hl~ICINOS [( N -4-Chlorophenyl)methanesulfinamidato]-
O'~/NOR Me R~ lix
R = H, X = CI
Dimer: [79272-54- I]. Bis[J.I- [N -( 4-chlorophenyl) methanesulfinamidato-N:O]] tetramethyldialuminum, lOCI. C18H2~hChN202S2 M 491.405 Colourless solid, air- and moisture-sensitive. Sol. py, CHCh, insol. pentane. Thought to exist as mixt. of conformational isomers.
Klerks, J.M. et aI, J. Organornet. Chern., 1981,214,1 (synth, ir, nrnr, crnr)
C9Hl~IO Dimethyl(2-methylphenolato )aluminum, lOCI
Dimethylaluminum 2-methylphenoxide [64470-63-9]
As (2-Chlorophenolato )dimethylaluminum, AI-l 00 14 with
M 164.183 Exists as mixt. of dimer and trimer. White air-sensitive
cryst. Dimer: C18H2~h02
Trimer: C27H39AI303
M 328.365
M 492.548 Pasynkiewicz, S. et aI, J. Organornet. Chern., 1977, 132, 191.
C9Hl~I02 (2-Methoxyphenolato )dimethylaluminum, lOCI
Dimethylaluminum 2-methoxyphenoxide
with
M 180.182 Mainly dimeric in soln. White air-sensitive solid. Dimer:
ClsHuAl:z04 M 360.364 Pasynkiewicz, S. et ai, J. Organomet. Chem., 1977,132,191
(synth, ir, pmr)
AI-10025 Dimethyl(N-phenylmethanesulfinamidato)aluminum As [(N-4-Chlorophenyl)methanesulfinamidato]
dimethylaluminum, AI-l0022 with
R=X=H
methanesulfinamidato-N:O) ]dialuminum, lOCI.
CIsH:zsAhN:zO:zS:z M 422.514 Colourless solid, air- and moisture-sensitive. Sol. CHCh, py, C6H6, insol. pentane. Thought to exist as mixt. of conformational isomers.
Klerks, 1.M. et ai, J. Organomet. Chem., 1981,214, I (synth, ir, nmr, cmr)
C 9HzIAIN4 AI-10026 Trimethyl(1,3,5, 7-tetraazatricyclo[3.3.1. 13,7]decane-NI)
aluminum, l1CI (Urotropin)trimethylaluminum. (H examet hylenetetramine) trimeth ylaluminum [83801-37-0]
M 212.273 Colourless air-sensitive solid (hexane). Sol. aromatic
hydrocarbons, spar. sol. hexane. Mp 163-1640 dec. See also Hexamethyl[w(l,3,5,7- tetraaza tricyclo [3.3.1.1 3,7] decane-Nl :N3) ] dialuminum, AI-I0042 and Nonamethyl[J.l3-(l,3,5,7- tetrazatricyclo[3.3.1.13,7]decane-Nl:N3:N5) ] trialuminum, AI-I0063 .
Krause, H. et ai, J. Organomet. Chem., 1982, 235, 253 (synth, pmr, ir)
C 9H z1AIS AI-10027 Diisobutyl(methanethiolato )aluminum
(M ethanethiolato )bis( 2-rnethylpropyl)alurninum, IICI. Diisobutylaluminum methanethiolate [85027-96-9]
M 188.306 Not isol. Catalyst for Beckmann rearrangements. Made
in situ (hexane). Maruoka, K. et ai, J. Am. Chern. Soc., 1983, lOS, 2831 (synth,
use)
6
M 252.191 Dimeric.
Dimer: Bis-J.l-(dimethylphosphinomethy/) tetrakis(dimethylphosphinomethyl)dialuminum. C 1sH 48Al:zP6 M 504.383 Colourless cryst.
Karsch, H.H. et ai, Phosphorus Sulfur, 1983,18,287. Karsch, H.H. et ai, J. Chem. Soc., Chem. Commun., 1984, 1415.
C9HZ7A1Sh Tris(trimethylsilyl)aluminum, lOCI
M 246.550 Colourless solid. Mp 600 dec.
AI-10029
I> Ignites spontaneously in air Et20complex: [75441-10-0]. l,l'-Oxybis[ethane]
tris(trimethylsilyl)aluminum. C13H37AIOSi3 M 320.673 Colourless air- and moisture-sensitive needles (pentane). Spar. sol. pentane.
TMEDA complex (2:1): [84929-13-5]. (N,N,N,N Tetramethylethanediamine)bis[tris(trimethylsilyl) aluminum]. C:Z7H7oAI:zN:zSi6 M 645.339 Colourless air- and moisture-sensitive needles (pentane).
Rosch, L. et ai, Angew. Chem.,lnt. Ed. Engl., 1977,16,480 (synth, nmr, ir)
Rosch, L. et ai, Angew. Chem.,lnt. Ed. Engl., 1979,18,60; 20, 551,582 (use)
Altnau, G. et ai, Tetrahedron Lett., 1980,4069; 1983,24,45 (use)
ROsch, L. et ai, J. Org. Chern., 1980, 195,47; 197,51 (use) Goebel, D.W. et ai, Organometal/ics, 1983,2,746 (deriv) Trost, B.M. et aI, J. Am. Chern. Soc., 1983, lOS, 4494 (use)
C9Hz7Ah04see AI-10030 Nonamethyl[J.l3-[ sulfato(2- )-0:0': 0"]]trialuminate(2-)
Tris(trimethylalurninoxo )oxosulfate(2-). Tris(trimethylaluminum)sulfate(2- )
C9H27AI3Cs204S M 578.125 Colourless cryst. (toluene).
Means, C.M. et aI, J. Am. Chern. Soc., 1984, 106, 7627 (synth, cryst struct)
CIOHuAI03W AI-10031 Tricarbonyl( "S-cyclopentadienyl)( dimethylaluminum)
tungsten
W W @ ' /, O C:&. b. C CO ~O r?
'A( / ,
Dimeric. Forms adducts with Me3N and Et20. Dimer: [11079-34-8]. Hexacarbonylbis(1]5-2,4-cyclopen
tadien-l-yl)bis( dimethylaluminum )ditungsten. Di -IJ. (tricarbonyl-1]5-cyclopentadienyltungsten-0,O') bis(dimethylaluminum). C2oH22A1206W2 M 780.053 Yellow air- and moisture-sensitive cryst. (toluene/methylcyclohexane). Ir Vco 1981, 1685, 1650 em-I.
Schrieke, R.R. el ai, J. Organornel. Chern., 1971,31, C46 (synth)
Conway, A.J. et ai, J. Chern. Soc., Dalton Trans., 1975,2499 (synth, ir, prnr, crysl struct)
CloH13AI03 AI-10032 [(2-Methoxycarbonyl)pbenolato ]dimethylaluminum
M208.192
MeO
Mainly monomeric. White solid, air- and moisture sensitive. Sol. C6H 6.
Pasynkiewicz, S. et ai, J. Organornet. Chern., 1977, 132, 191 (synth, ir, prnr)
CloHI~INOS AI-10033 Dimethyl[ N -( 4-methylphenyl)methanesulfinamidato]
aluminum Dimethyl[N -(p-tolyl)methanesuIJinamidato] aluminum As [(N-4-Chlorophenyl)methanesulfinamidato]-
dimethylaluminum, AI-I 0022 with
R = H, X = CH3 M 225.284 Monomer-dimer equilibrium. Evidence found for
conformational isomers. Dimer: [79272-53-0]. Tetramethylbis[lJ.- [N -( 4-
methylphenyl)methanesuIJinamidato-N:O ]] dialuminum, lOCI.
C2oH32AlzN202S2 M 450.568 Colourless solid; air- and moisture-sensitive. Sol. CHCb, Py, insol. pentane.
Klerks, J.M. et ai, J. Organornet. Chern., 1981,214, 1 (synth, ir, nrnr, crnr)
7
(Diallylamino )diet hylaluminum [77924-60-8]
M 181.256 Molecular complexity not reported. Reagent for
aminolysis of epoxides. Used in situ. Overman, L.E. et ai, Tetrahedron Lett., 1981,22,195 (use)
CIIH1SAICI AI-10035 Chloromethyl(pentamethylcyclopentadienyl)aluminum Updated Entry replacing AI-00390
M 212.698 Dimeric with cyclopentadienyl ring 1]3-bound. Dimer: [72303-53-8]. Di-IJ.-chlorodimethylbis[(J ,2,3-1])-
1,2,3,4,5-pentamethyl-2,4-cyclopentadien-l-yl] dialuminum, lOCI. Colourless cryst. (hexane). Spar. sol. C6H 6, toluene, hexane. Bpo.ool 800 subl. Extremely sensitive to air and moisture, solid and solns. turn purple.
Schonberg, P.R. et ai, J. Arn. Chern. Soc., 1979, 101,7726 (synth, rns, crnr, prnr, cryst struet)
Schonberg, P.R. et ai, Organornetallics, 1982, I, 799 (crysl Slrucr)
CIIH1SAIN AI-10036 Diethyl(N-methylanilinato)aluminum,8CI
M 191.251 Colourless needles, air- and moisture-sensitive. BPo.005
1900 •
Neumann, W.P., Justus Liebigs Ann. Chern., 1963, 667, 1 (synth)
CUH1SAINOS AI-10037 [ N -(2,6-Dimetbylphenyl)methanesulfinamidato]
dimethylaluminum, AI-I 0022 with
R = CH3, X = H
mational isomers.
Dimer: [79272-50-7]. Bis[p.-[N-(2,6-dimethylphenyl) met hanesulfinamidato-N:O]] tetramethyldialuminum, lOCI.
C12H~hN202S2 M 478.622 Colourless solid; air- and moisture-sensitive. Sol. Py, CHCh, insol. pentane.
Klerks, I.M. et ai, J. Organomet. Chem., 1981,214, 1 (synth, ir, nmr, cmr)
CnH31AICiJP3W AI-10038 Chloro( dichloromethylaluminum)-
methylidynetris( trimethylphosphine )tungsten, lOCI
Me/ 'C~ I 'PMeJ
Cocrystallises with Chloro( chlorodimethylaluminum) methylidynetris(trimethylphosphine)tungsten, AI- 10044.
Churchill, M.R. et ai, [norg. Chem., 1981, 20, 3392 (synth, struct)
C12H20AICI AI-10039 Chloroethyl(pentamethylcyclopentadienyl)aluminum As Chloromethyl(pentamethylcyclopentadienyl)aluminum,
Dimer: [81457-43-4]. Di-p.-chlorodiethylbis[(I,2,3-71)- 1,2,3,4,5-pentamethyl-2,4-cyclopentadien-l-yl] dialuminum. C24H40AI2Ch M 453.449 Colourless air- and moisture-sensitive cryst. Sol. C6H6,
toluene, THF, EtzO, spar soL hexane. Bp 58 0 subl. Schonberg, P.R. et ai, Organomelu.l/ics, 1982, I, 799 (synth,
pmr)
aluminum As [(N-4-Chlorophenyl)methanesulfinamida to]
dimethylaluminum, AI-l 0022 with
trimethylphenyl)methanesulJinamidato-N:O]] dialuminum, lOCI.
C24H40AhN202S2 M 506.675 Colourless solid; air- and moisture-sensitive. Sol. Py, CHCl3, insol. pentane.
Klerks, J.M. el ai, J. Organomet. Chem .. 1981,214, I (synth, ir, nmr, cmr)
8
AI-10041
Not isol. Molecular complexity not reported. Reagent for regio- and stereoselective synth. of allyl- and vinyl silanes. Useful in synth. of steroidal side chains. Used in situ.
Hayami, H. et ai, J. Am. Chem. Soc., 1983, 105,4491 (use) Okuda, Y. et ai, Tetrahedron Lett., 1983,24,2015 (use)
C12H~hN4 AI-10042 Hexamethyl[p.-(1,3,5, 7 -tetraazatricycio[3.3.1.13, 7]decane
Nl:N3)]dialuminum,1I0 Urotropinbis( trimet h ylaluminum). Hexamethylenetetraminebis(trimethylaluminum) [83801-38-1]
hydrocarbons, spar. sol. hexane. Mp 143 0 •
Krause, H. el ai, J. Organomet. Chem., 1982,235,253 (synth, ir, pmr)
C12H32AIP49 AI-10043 Tetrakis[ (dimethylphosphino )methyl]aluminate(l-), lIeI
M 327.261 (ion) Li salt:
(MezPCHz)4AI9
C12H32AlLiP4 M 334.202 White air- and moisture-sensitive powder. Spar. sol. EtzO, THF. May be polymeric. 31p nmr 0 -50.2 ppm (reI. 85% H 3P04).
Karsch, H.H. et ai, J. Chem. Soc., Chem. Commun., 1984,1415 (synth)
C 12H34AIChP3 W AI-10044 Chloro( chlorodimethylaluminum)-
methylidynetris( trimethylphosphine )tungsten [76642-47-2] As Chloro( dichloromethylaluminum)
methylidynetris( trim ethyl phosphine )tungsten, Al- 10038 with
X = Me, Y = Cl
M 553.059 V. air- and moisture-sensitive red prisms (toluene). Sol.
toluene spar. sol. pentane. Churchill, M.R. el ai, [norg. Chem., 1981, 20, 3392 (synth, crysl
struct) Sharp, P.R. el ai, J. Am. Chem. Soc., 1981, 103,965 (synth) Holmes, S.J. et ai, Organometallics, 1984,3,476 (pmr, emr, P-
31 nmr, AI-27 nmr)
phosphinimidic amidato-N,N']aluminum, lOCI
[76830-43-8]
M 350.642 Colourless liq., air- and moisture-sensitive. BpO.Ol 90°. Cowley, A.H. et ai, J. Am. Chem. Soc., 1981,103, 1575 (synth,
pmr, cmr, P-31 nmr)
CI2H3~ISi4e Tetrakis(trimethylsilyl)aluminate(l-), lOCI
M 319.740 (ion) Na salt: [73836-41-6]. C12H~INaSi4 M 342.730
AI-10046
Colourless cryst. Mp 105°. BpO.OOOOl 140° subl. Forms complexes with 8Et20 (Mp 59°), 9THF (Mp 101°), 3DME (Mp 208°).
K salt: [73728-15-1). C12H~IKSi4 M 358.838 Colourless solid. Mp 64°. BpO.OOOOl 160°. Forms com plexes with 3Et20 (Mp 48°), 2THF (Mp 0°), 3DME (Mp 124°).
Rosch, L. et ai, J. Organomet. Chem., 1980, 195,47; 197, 51 (use)
Rosch, L. t!Htl, Z. Naturf~ch., B, 1980,35, 195 (synth, pmr, ir)
CI2H~140~2ee AI-10047 Dodecamethyl[#'4-[ monothiosulfato(2-)-0: 0': 0" :S]]
tetraaluminate(2-), lOCI Tris( trimethylaluminiooxo)( trimethylaluminosulfido) sulfate(2- )
M 400.461 (ion) Di-Cs salt: [66349-95-9]. C12H~14Cs20~2 M 666.272 White powder, v. air- and moisture-sensitive. Mp 130- 160° dec. Reversible loss of AlMe3 occurs> I 70°.
Aeissen, H. et ai, Chem. Ber., 1978, 111,480 (synth, ir, raman)
CI2H~~o~ee Dodecamethyll#'4-[sulfato(2-)-0:0': 0": 0''']
tetraaluminate(2-), lOCI Tetrakis(trimethylaluminoxo )sulfate(2-)
M 384.400 (ion) Di-K salt: [87861-92-5]. C12H~14K204S M 462.597
AI-10048
White solid; v. air- and moisture-sensitive. Forms solvate with p-xylene.
Di -Cs salt: [66349-94-8].
AI-18045 - AI-l0052
C12H~14Cs20~ M 650.211 White powder; v. air- and moisture-sensitive. Mp 130- 160° dec. Reversible loss of Al Me3 occurs> 1 70° .
Aeissen, H. et ai, Chem. Ber., 1978, 111,480 (synth, ir, raman) Rogers, R.D. et aI, Organometallics, 1984,3, 271 (cryst strucr)
CI2H3~140~2ee AI-10049 [#'4-[Dithionato(2-)]]dodecamethyltetraaluminate(2-), lOCI
Tetrakis(trimethylaluminiooxo )dithionate( V)
[(Me3AIOhS(O)-S(O)(OAIMe3h)99
M 448.459 (ion) Di-Cs salt: [66349-83-5]. C12H~14Cs20~2 M 714.270 White powder, extremely air- and moisture-sensitive. Mp 130-160°. Reversible loss of AlMe3 occurs> 170°.
Aeissen, H. et aI, Chem. Ber., 1978, 111, 480 (synth, ir, raman)
C13HI7AhCIFe AI-10050 Chloro(ferrocenediyl)trimethyldialuminum
M 318.540 Dimeric.
Fe f ~ AlV' © /\ Al-Me
C26H34Al4Cl2Fe2 M 637.081 V. air-sensitive cryst. (toluene). Sol. aromatic hydrocarbons.
Atwood, J.L. et aI, J. Chem. Soc., Chem. Commun., 1976,536 (synth, pmr, cryst Slruct)
C13H27AIPRh AI-10051 (",5_ 2,4-Cyclopentadien-l-yl)( ",2-
ethene)( trimethylaluminum)( trimethylphosphine )rhodium [90413-14-2]
M344.217 Dissociation of AlMe3 is rapid on the nmr time scale even
at -80°. Rare example of an unbridged aluminum transition-metal compd. Yellow solid. Sol. C6H 6•
Mayer, J.M. et aI, Organometallics, 1984,3,1292 (synth, ir, pmr)
C13H37AICIP3W Chloro(methylidyne)(trimethylaluminum)
M 532.641 Characterised by nmr. Red solid (toluene/pentane), v.
air-sensitive. Sol. toluene, spar. sol. pentane. Sharp, P.R. et aI, J. Am. Chem. Soc., 1981,103,965. Holmes, S.l. et aI, Organometallics, 1984,3,476 (synth, pmr,
cmr, P-31 nmr)
Dimethylaluminum diphenylphosphide [85004-95-1 ]
M 242.236 Dimeric.
Dimer: [87578-35-6]. Bis[JL-(diphenylphosphino)] tetramethyldialuminum, lie/. C:zsH31AhP1 M 484.471 Colourless cryst. (C6H 6). Sol. C6H 6, spar. sol. EhO. Mp 230°. BpO.OOI 160° subl.
t> Inflames in air Coates, G .E. et aI, J. Chem. Soc., 1963, 233 (synth) Beachley, O.T. et aI, Organometallics, 1983,2, 796 (synth, pmr,
ir)
AI-H-Ti
Dimeric. Apparently identical with compd. earlier char acterised as [(CsHshTiAlEt2lz. Several related compds. also prepd.
Dimer: [39414-10-3]. Bis(TJ5_2,4 -cyclopentadien-I-yl) bis[JL- [J -TJ:I ,2,3,4,5-TJ)-2,4-cyclopentadien-I ylidene]] bis( diethylaluminum )di -JL-hydrodititani um, 9Cl. C:zsH42AhTh M 528.363 Catalyst for polymerisation of alkenes. Red cryst. (heptane). Mp 169-171 ° dec. Diamagnetic.
Natta, G. et ai, CA, 1960,54, 17357 (synth) Corradini, P. et ai, Inorg. Chern., 1967,6,601 (eryst struet) Tebbe, F.N. et ai, J. Chern. Soc., Chern. Cornrnun., 1973,227
(synth, nrnr) Mach, K. et ai, J. Organornet. Chern., 1984,269,39 (synth, use.
nrnr, crnr)
[79649-18-6]
M 352.095 Polym. catalyst. Violet cryst. (Et20/pentane). Sol. Et20.
V. air sensitive. Other adducts in place of Et20 known. Bulychev, B.M. et aI, J. Organornet. Chern., 1979, 179, 263
(synth, esr, use) Bulychev, B.M. et ai, Transition Met. Chern., 1981,6, 32. Lobkovskii, E.B. et aI, J. Organornet. Chem., 1984,270, 45
(synth, eryst struct)
M 297.277 Not isol. Catalyst for Beckmann rearrangements. Used in
situ (hexane). Maruoka, K. et ai, J. Arn. Chern. Soc., 1983, 105, 2831 (synth,
use)
Dimer: [81457-44-5]. Di-/-L-chlorobis(2-methylpropyl) bis[ (J ,2,3 -TJ)-I ,2,3,4,5-pentamethyl-2,4-cyclopenta dien-I-yl] dialuminum. C:zsH4sAhCI2 M 509.556 Colourless air- and moisture-sensitive cryst. So!. C6H6,
toluene, hexane. 8p 95° sub!. (in vacuo). Schonberg, P.R. et ai, Organornetallics, 1982,1, 799 (.~ynth,
prnr, rns, eryst struet, emr)
C14H3~IN2PSi AI-10058 N,N' -Di- tert -butyl- P -methyl-P -( trimethy lsilyl)
phosphimidic amidato- N, N' ]dimethylaluminum [N,N'-Bis(l,l-dimethylethyl)-P-methyl-P (trimethylsilyl)phosphinimidic amidato-N ,N'] dimethyl aluminum, lOCI
phosphinimidic amidato-N,N']aluminum, AI-\ 0045 with
M 318.493 Colourless liq., air- and moisture-sensitive. Sol. hydrocar
bons, CH2CIz. BpO.OI 115°. Cowley, A.H. et ai, J. Arn. Chern. Soc., 1981, 103, 1575 (synth,
prnr, crnr, P-31 nrnr)
methanetetraylmethylbis( trimethylphosphine )tungsten, lOCI [79255-12-2]
M 540.660 Pale-yellow cryst. (chlorobenzene/pentane). Fairly air
and moisture-sensitive. Sol. toluene, spar. sol. pentane. Dec. in air to brown powder in ca. 30 min.
Churchill, M.R. et ai, Inorg. Chern., 1981, 20, 4119 (synth, cryst struct)
Holmes, S.l. et ai, Organornetal/ics, 1984,3,476 (synth, prnr, crnr, AI-27 nrnr, P-31 nrnr)
CJsH17AICI2N2S AI-10060 [ N,N' -Bis( 4-chlorophenyl)methanesulfinimidamidato]
dimethylaluminum
R N ....... S ...... N R Me, I \ ....... Me
....... AI AI, Me \ I Me
OR N ...... f ....... N';QR ~ R Me R h
x-' ~ X
Dimer: [79292-32-3]. Bis[1l-N,N' -bis( 4-chlorophenyl) methanesulfinimidamidato-N:N'] tetramethyldialuminum, lOCI. C30H34AI2CI4N4S2 M 639.614 Colourless cryst. (hexane). Sol. CHCh, CH2CI2, C6H6, toluene, spar. sol. pentane. Thermally unstable, slowly becomes dark at 20°. Moisture-sensitive.
t> Pyrophoric Klerks, 1.M. et ai, J. Organornet. Chern., 1981,214, I.
CJsHu,AIN AI-10061 Diisobutyl( N -methylanilinato )aluminum
N -Diisobutylaluminum-N -methylaniline
(C6H6/pentane). Mp 110-114° dec.
CJSH37AICI02P3W AI-10062 Carbonylchloro[p-( f/2-ethynolato-0)]( trimethylaluminum}
tris( trimethylphosphine )tungsten [81371-73-5]
Pco 1960, 1615 cm- l .
Churchill, M.R. et ai, Organornetallics, 1982,1,767 (synth) Holmes, S.T. et ai, Organornetallics, 1984,3,476 (synth, prnr,
crnr, P-31 nrnr)
NI:N3:N5)jtrialuminum,lIeI Urotropintris(trimethylaluminum). Hexamethylenetetraminetris(trimethylaluminum) [83808-65-5]
hydrocarbons, spar. sol. hexane. M p 219° dec . Krause, H. et ai, J. Organornet. Chern., 1982, 235, 253 (synth,
ir, prnr)
CJ6H20AIN (l,l-Diphenylmethylenimine)trimethylaluminum
(Diphenylketimine)trimethylaluminum [ 16522-15-9]
M 253.322
AI-10064
White needles (hexane). Air- and moisture-sensitive. Mp 76-76.5°. Dec. on heating to Al-00548.
Wade, K. et ai, J. Chern. Soc. (A), 1967, 1339 (synth, ir)
AI-10065 Bis(dimethylaluminum)tetra-wpropynylberyllium, lOCI
M 279.341
Pale-yellow solid. Sol. THF, dioxan, Et3N, insol. hydro carbons. Mp l(i2-165°. Ir,,~ 2146 cm-I.
t>Toxic Starowieyski, K.B. et ai, J. Organomet. Chem., 1981,215,151
(synth, ir, nmr)
[79572-41-1]
M 294.634 White solid. V. sol. dioxan, spar. sol. THF, toluene, insol.
hexane. Mp 189-196° dec. Ir,,~ 2136 cm-I. Starowieyski, K.B. et ai, J. Organomet. Chem., 1981,215,151
(synth, ir, pmr)
(H3ChC /" /" CCCH3h 0 0 CI 00 H3C ~ ~(CH3)3 (H3C)3J # CH3
M 296.815 Dimeric. Dimer: Bis[2,6-his(1 ,1-dimethylethyl)-4-methylpheno
lato] -di -JL-chlorodimethyldialuminum. C32Hs2AhCI202 M 593.631 White air-sensitive cryst. (cyclohexane). Sol. C6H6,
cyclohexane. Skowronska-Ptasinska, M. et ai, J. Organomet. Chem., 1978,
160,403 (synth, pmr)
M 375.140
AI-10068
Not isol. Reagent for conversion of allyl acetates to allylstannanes and allyl alcohols, and of I-alkynes to vinylstannanes. Used in situ in THF.
Hibino, J. et ai, Tetrahedron Lett., 1984,25,2151 (use) Trost, B.M. et ai, J. Am. Chem. Soc., 1984, 106,6835 (use)
12
lC6H6 (C6H 6).
Atwood, J.L. et ai, Organometallics, 1983,2,985 (synth, cryst struct)
AI-10070 [N,N' -His( 4-metbylpbenyl)metbanesulfinimidamidato]
Dimer: [79292-31-2]. Bis[JL-[N,N'-Bis(4- methylphenyl)methanesulJinimidamidato-N:N']] tetramethyldialuminum. C34H46A,hN4S2 M 628.847 White solid (hexane); v. sensitive to hydrol. Sol. CHCI3, CH2CIz, C6H 6, spar. sol. pentane. Slow dec. at 20° to yellow-brown solid.
I> Pyrophoric Klerks, J.M. et ai, J. Organomet. Chem., 1981,214,1 (synth)
C17H 3sAIOSi AI-10071 Dimethyl[ 4-methyl-4-(trietbylsilyl)oxy ]-l-octynyl-C,O]
aluminum, 9CI [59200-28-1]
Me2AlC=CCH2C(OSiEt3)CH3(CH2)3CH3
M 310.530 Reagent for prostaglandin synth. Used in situ. Collins, P.W. et ai, Tetrahedron Lett., 1975,4217 (synth, use)
ClsHlsAl Tripbenylaluminum Updated Entry replacing AI-00616
Aluminum triphenyl. Triphenylalane [841-76-9]
Dimeric. Cryst. (toluene). Mp 229-232°, 126-130° (Et20 solvate).
I> Dec. violently in the presence of air and moisture Me3CCN complex: Triphenyl(pivalonitrile)aluminum.
(tert-Butyl cyanide )triphenylaluminum.
CZ3H~IN M 341.431 Colourless, air-sensitive solid (C6H6). M p 114°. At 190-200° gives [(H3ChCCPh=NAIPh2]n'
Wittig, G. et ai, Justus Liebigs Ann. Chern., 1957,606, 13 (synth)
Org. Synth., Coll. Vol., 5, I I 16 (synth) Mole, T., Aust. J. Chern., 1963, 16,794 (synth) Surtees, J.R., Rev. Pure Appl. Chern., 1963, 13, 91 (rev) Jennings, J.R. et ai, J. Chern. Soc., 1965,5083 (synth, ir, prnr,
deriv) ShurvelI, H.F. et ai, Spectrochirn. Acta, Part A, 1967,23,2925
(ir) Malone, J.F. et ai, J. Chern. Soc., Dalton Trans., 1972,2646
(cryst struct) Dewar, M.J.S. et ai, J. Chern. Soc., Dalton Trans., 1973, 238 I
(nqr) Glockling, F. et ai, J. Chern. Soc., Dalton Trans., 1973, 1424
(rns) Streck, R., J. Org. Chern., 1974,71,181 (synth) Bretherick, L., Handbook of Reactive Chemical Hazards, 2nd
Ed., Butterworths, London and Boston, 1979, 735. Sax, N .1., Dangerous Properties of Industrial Materials, 5th
Ed., Van Nostrand-Reinhold, 1979, 1067. Hazards in the Chemical Laboratory, (Bretherick, L., Ed.), 3rd
Ed., Royal Society of Chemistry, London, 1981, 525.
C1sHzzAIN AI-10073 2,3-Dihydro-l-isobutyl-4-methyl-2-phenyl-l H-2,l-benzaza
Dimer: C36H44AIzNz M 558.720 Colourless cryst. (decalin). Spar. sol. hexane, dec. by alcohols, H20. Mp 179-180°.
Hoberg, H., Justus Liebigs Ann. Chern., 1971,746,86 (synth)
ClsH31AhNlee AI-10074 Hexamethyl[I'-[l,l' ,4,4' -tetrahydro-4,4' -dimethyl-4,4' -bi
pyridinato(2-)-N:N']]dialuminate(2-), 110 1,1' -Bis(trimethylaluminyl)-I ,1',4,4' -tetrahydro-4,4' dimethylbipyridate(2- )
[Me3AI-N~N_AIMe3Iee ~
CZ6HszAIzLiNzOz M 485.613 Red oil.
Dorogy, W.E. et ai, Inorg. Chirn. Acta, 1983,73,31 (synth, prnr, crnr, AI-27 nrnr, ir)
13
ytterbium [93085-13-3]
Me/ Me
M 637.983 Contains significant AI-C· Yb interactions. Polymerises
C2H4 at 20°, 12 atm. Yellow plates. Sol. pentane. Dia magnetic.
BoncelIa, J.M. et ai, Organornetallics, 1985,4,205 (synth, cryst struct, nrnr, ir, rns)
C19Hz~IN AI-10076 [N-(2,6-Dimethylbenzyl)anilinato ]diethylaluminum, SCI
N -Diethylaluminum-N - [2,6-dimethylbenzyl] aniline [32496-08-5]
M 295.403 Dimeric in C6H6.
Dimer: C38HszAIzNz M 590.805 Colourless cryst. (hexane). Spar. sol. hexane, dec. in alcohols, H20. Mp 129-131°. At 160° gives AI-00598.
Hoberg, H., Justus Liebigs Ann. Chern., 1971,746,86 (synth, ir, rns)
C19Hz7AINzS AI-10077 [ N,N' -Dis(2,6-dimethylphenyl)methanesulfinimidamidato}
dimet hylpheny l)met hanesulfini midamidato-N:N '] tetramethyldialuminum, lOCI.
C38HS4AIzN4Sz M 684.954 White solid (hexane), V. sensitive to hydrol. Sol. CHCh, CH2CI2, C6H6, spar. sol. pentane. Slow dec. at 20° to yellow-brown solid.
I> Pyrophoric Klerks, J.M. et ai, J. Organornet. Chern., 198 I, 214, I.
AI-10078 l,2-Dibydro-l-acenapbtbylenyldiisobutylaluminum Updated Entry replacing AI-00647
(1,2-Dihydro-I-acenaphthylenyl)bis(2-methylpropyl) aluminum,9CI. I-Acenaphthenyldiisobutylaluminum [51754-77-9]
R = CH2CH(CH3h M 294.415 Reacts with carbonyl compds. stereoselectively. Formed
and used in situ. Sol. heptane. Not isolated, structure deduced from hydrolysis and carbonation.
Eisch, J.J. et ai, J. Organornet. Chern., 1974,64,41 (synth) Eisch, J.J., Comprehensive Organornet. Chern., 1982,1,606
(nrnr) Eisch, J.J. et ai, J. Org. Chern., 1984,49,4631 (synth)
C2oH28AIN AI-10079 Dibutyl( dipbenylamino )aluminum
N -(Dibutylaluminum)diphenylamine
M 309.429 Colourless plates (pentane/C6H6). Turns red in air. Mp
85-86°. Neumann, W.P., Justus Liebigs Ann. Chern., 1963, 667, I
(synth)
with
moisture-sensitive. Sol. hexane, C6H6. Mp 141-143°. Dimer: Bis-/l-(diphenylphosphino)
tetrakis(trimethylsilylmethyl)aluminum. C4oH64AhP2Si4 M 773.198
Beachley, O.T. et 01, Organometallics, 1983, 2, 796 (synth, pmr, ir)
14
AJ-10078-AJ-10083
derivs. or aromatic N-heterocycles. Dimer:
C42H60A12N2 M 646.912 Colourless prisms (pentane). Dec. in H20. Mp 106- 109°.
N -Benzylideneaniline complex: C34H41AlN2 M 504.693 Orange-red hexagonal prisms (pentane). Sol. C6H6, spar. sol. pentane, dec. in H20, alcohols.
Neumann, W.D., Justus Liebigs Ann. Chern., 1963,667, I (synth, deriv)
Hoberg, H., Justus Liebigs Ann. Chern., 1971,746,86 (synth)
C22H32AIN AI-10082 Diisobutyl[ N -(2-metbylbenzyl)anilinato ]aluminum
[32496-00-7] As (N-Benzylanilato )diisobutylaluminum, AI-l 0081 with
Rl = Me, R2 = H
M 337.483 Dimeric in C6H6 and from ms data. Dimer:
C44H64AhN2 M 674.966 Colourless cryst. (pentane). Dec. in H20. Mp 138- 140°.
Hoberg, H., Justus Liebigs Ann. Chem., 1971,746,86 (synth)
C23H24AICr06P AI-10083 Pentacarbonyl( dimethylaluminum )[/l-[ 4-( diphenylphosphino)
I-butanolato-O:P]]chromium,IICI [85883-61-0]
M 506.390 Molecular complexity not known. Forms a glass. Brown
yellow glassy solid, air- and moisture-sensitive. Sol. ar omatic hydrocarbons, ethers, spar. sol. hexane. Mp 70°. Glass forms at 48-50°.
Tessier-Youngs, C. et 01, Organometallics, 1983,2,1128 (synth, ir, pmr)
CuHatAlN - CzsHzaAlCrOaP
0r'N"'AI[CHl CH(CH3hh
Colourless cryst. Forms coloured complexes with azomethine derivs. or aromatic N-heterocycles.
Neumann, W.P., Justus Liebigs Ann. Chern., 1963,667,1 (synth, derivs)
C1Jll49AIOSi AI-10085 Bis(l-metbylpropyl)( 4-metbyl-4-( trietbylsilyl)oxy ]-1-octenyl
GO]aluminum,9CI
[(H3ChCHCH2]2AICH=CHCH2C(OSiEt3) CH3(CH2hCH3
M 396.707 (E)-form [59200-29-2]
Reagent for prostaglandin synth. Used in situ. Collins, P.W. et ai, Tetrahedron Lett., 1975,4217 (synth, use)
C14H17A1N4 AI-10086 5,I4-Dibydro-6,8,15, 17-tetrametbyldibenzo[ b,ill,4,8, 11]
tetraazacyclotetradecinato( ethyl)aluminum
M 398.486 Orange cryst., stable to H 20. Photosensitive. Stable to at
least 300°. Goedken, V.L. et ai, J. Chern. Soc., Chern. Cornrnun., 1983,
1453 (synth, eryst struct)
C~39AI Tri-l-octynylaluminum, 9CI
AI-10087
Pappo, R. et ai, Tetrahedron Lett., 1972, 2627 (synth, use)
15
AJ-10084-AJ-10090
metbylpbospbine]-P:P']tetra-,,-bydrodimanganese, 110
[87450-49-5]
M 772.462 May dissoc. in soln. Yellow cryst. Sol. pet. ether. Girolami, G.S. et ai, J. Am. Chern. Soc., 1983, 105,6752 (synth,
prnr, ir, cryst struct)
Diphenylaluminum phenyl(p-bromophenyl)ketimide
McDonald, W.S., Acta Crystal/ogr., Sect. B, 1969,25,1385 (synth, eryst struct)
ClsH~ICr06P AI-10090 Pentacarbonyl( dietbylaluminum)(,,-[ 4-( dipbenylpbosphino)
I-butanolato-O:P]]chromium,IICI [85883-62-1 ]
M 534.444 Monomer-dimer equilibrium in soln. Prob. dimeric in sol
id state by analogy with Pentacarbonyl[bis(trimethylsilylmethyl)aluminum] [It" [4-( diphenylphosphino )-I-butanolato-O:P]] chromium, AI-I0097 . Tan coloured air-sensitive solid. Sol. aro matic hydrocarbons, ethers, spar. sol. hexane. Mp 159- 160°.
Tessier-Youngs, C. et ai, Organornetallics, 1983, 2, 1128 (synth, ir,prnr)
CzsH~IJMol AI-10091 Bis(~-2,4-cyciopentadien-l-yl)bisfp3-[(1-,,:1,2,3,4,S-,,)-2,4-
@<')@ AI
/ \ Me Me
V. air- and moisture-sensitive orange cryst. (toluene). Spar. sol. C6H6, toluene. Reacts with CO2 followed by HBr to give [(CsHshMo(CO)Br]+ and with CH2=CHCH2Br to give [(CsHshMo(7r-C3HS)]+'
Forder, R.A. et ai, J. Chern. Soc., Chern. Cornrnun., 1973,426. Forder, R.A. et ai, Acta Crystallogr., Sect. B, 1974,30,2312
(synth, eryst struct) Benfield, F.W. et ai, J. Less Common Metals, 1974,36,187
(synth, props) Rettig, S.l. et ai, Acta Crystallogr., Sect. B, 1974,30,666 (eryst
struct)
M 441.427 Dimeric.
Ph I R PPh2
Dimer: [86225-24-3]. Bis[p.- [N -(diphenylphosphino) P,P-diphenylphosphinous amidato-N:P]] tetramethyldialuminum, Ilei. Bis[bis(diphenylphosphino) - amidatodimethylaluminum ]. CszHszAlzNzP4 M 882.854 Colourless solid (C6H6), air- and moisture-sensitive. Sol. THF, spar. sol. C6H6, toluene, hexane. Mp 190°.
Schmidbaur, H. et aI, Chern. Ber., 1983, 116, 1403 (synth, prnr, P-31 nrnr, cryst struct)
16
ylidene]]bis(dimethylaluminum)bis(methylaluminum) dimolybdenum Dimolybdenumbis-p.- [meth ylaluminumdi[p.-( 715:711)
cyclopentadienyl]dimethylaluminum] [50643-75-9]
M 646.361 V. air- and moisture-sensitive yellow cryst. Insol. Forder, R.A. et ai, J. Chern. Soc., Chern. Cornrnun., 1973,426;
Acta Crystallogr., Sect. B, 1974,30,2312 (synth, eryst struct)
CzsH30AINPz AI-10094 [ N-(Diphenylphosphino)-P ,P-diphenylphosphinous
amidato ]dimethylaluminum, AI-l 0092 with
M 469.481 Dimeric.
Dimer: [86225-26-5]. Bis[p.- [N -(diphenylphosphino) P,P-diphenylphosphinous amidato-N:P]] tetraethyldialuminum, IIC/.
CS6H60AlzNzP4 M 938.962 Colourless solid (toluene). Sol. THF, spar. sol. C6H6, toluene, hexane. Mp 179° dec.
Clemens, D.F. et aI, [narg. Chern., 1966,5, 527 (synth, ir) Schmidbaur, H. et aI, Chern. Ber., 1983, 116, 1403 (synth, prnr,
P-31 nrnr)
aluminum ][p.-( diphenylphosphino) ]chromium Pentacarbonyl[(N,N-dimethylmethanamine)- bis[ (trimethylsilylmethyl)aluminum] [p. (diphenylphosphino) ] chromium, IIC/
[84558-22-5]
(OC)sCrPPh2AI(CH2SiMe3)2NMe3
C28H41AIMg03' AI-10096 [#,-(9, 1 0-Dibydro-9, 10-
antbracenediyl)](bydrodimetbylaluminum) tris(tetrabydrofuran)magnesium, 110 Tris( tetrah ydrofuran )magnesi um-~-( 9,1 O-dihydro- 9,lO-anthrylene)hydrodimethylaluminate [89738-00-1 ]
R = Me
M 476.917 THF content of solid uncertain. Air- and moisture
sensitive citron yellow cryst. (THF) giving green soln. in THF. Sol. THF.
Lehmkuhl, H. et ai, Chern. Ber., 1984, 117, 389 (synth, prnr, crnr)
C29H40AICr06PSh AI-10097 Pentacarbonyl[bis( trimetbylsilylmetbyl)aluminum ][~-[ 4-( di
pbenylpbospbino )-l-butanolato-O:P]]cbromium
M 650.754 Monomer-dimer equilibrium in soln. Dimer: [85883-63-2]. Bis[bis[(trimethylsily/)methyl]
aluminum]decacarbonylbis[~r[4-(diphenylphos phino )-l-butanolato-O:O:P]] dichromium, IICI.
CssHsoAIzCr2012P2Si4 M 1301.507 Tan coloured air-sensitive solid. Sol. aromatic hydrocarbons, ethers, mod. sol. hexane. Mp 102.5- 103°.
Tessier-Youngs, C. et ai, Organornetallics, 1983,2, 1128 (synth, ir, nrnr, cryst struct)
C30H4sAIMg03 AI-10098 (DietbylbydroaluminumX#'-(9, 1 0-dibydro-9, 1 0-
antbracenediyl)]tris( tetrabydrofuran)magnesium, IICI Tris(tetrahydrofuran)magnesium-~-(9,lO-dihydro- 9,1 O-anthrylene )diethylhydroaluminate [89738-01-2] As [~-(9,10-Dihydro-9,10-
M 504.970 THF content of solid uncertain. Air- and moisture
sensitive yellow cryst. (THF) giving green soln. in THF. Sol. THF.
Lehmkuhl, H. et ai, Chern. Ber., 1984,117,389 (synth, pmr, crnr, cryst struct)
17
dipbenylaluminum, SCI
M 529.671 Amorph. white solid or cryst. + C6H6(C6H6)' Rapidly
dec. by H20. Mp 222-224°. Schmidbaur, H. et ai, Chern. Ber., 1967, 100, 1016 (synth, ir,
prnr)
metbylpropyl)aluminum ]tris( tetrabydrofuran)magnesium, 110 Tris(tetrahydrofuran)magnesium-~-(9,lO-dihydro- 9,1 O-ant hrylene) h ydridodiisobuty I aluminate [89738-02-3] As [w(9,10-Dihydro-9,10-
anthracenedi yl) ) (h ydrodimeth ylal umin um) tris( tetrahydrofuran)magnesium, AI-l 0096 with
R = -CH2CH(CH3h M 561.077 THF content of solid uncertain. Air- and moisture
sensitive yellow-green cryst. (THF) giving green soln. in THF. Sol. THF.
Lehmkuhl, H. et ai, Chern. Ber., 1984, 117, 389 (synth, prnr, crnr)
C34HSsAI02 AI-10101 Isobutylbis(2,6- tert -butyl-4-metbylpbenolato )aluminum
Bis[2,6-bis(J ,1-dimethylethy/)-4-methylphenolato] (2- methylpropyl)aluminum,9cl. Isobutylaluminum di(2,6- tert-butyl-4-methylphenoxide) [56252-57-4)
RZO"""" C(CH3)3 (H3ChCO"""" RZ #0 0 #
(H3ChC ~ / C(CH3h Al I RI
Rl = -CHzCH(CH3h,Rz = CH3
Sol. C6H6, toluene, cyclohexane. Starowieyski, K.B. et ai, J. Organornet. Chern., 1975,90, C43
(synth) Skowrofiska-Ptasifiska, M. et ai, J. Organornet. Chern., 1978,
160,403 (prnr)
aluminum, AI-IOIOI with
Sol. C6H6, toluene, cyclohexane. Skowronska-Ptasiiiska, M. et ai, J. Organomet. Chem., 1977,
141, 149 (synth, pmr)
aluminum, 9CI [36661-58-2]
Al [O=CCH(OTHP)CH2(CH2)3CH3] 3
M 654.905 Reagent for prostaglandin synth. Used in situ. Pappo, R. et ai, Tetrahedron Lett., 1972, 2627 (synth, use)
C4:zH..sAINPSi AI-10104 Triphenylaluminum p,p,P-tris(4-methylphenyl)-N-trimeth
ylsilylphosphineimine Triphenylaluminum N -trimethylsilyltri-p tolylphosphineimine
M 649.865 Monomeric in C6H6. Solid (C6H6). Mp 195-2020 dec. Schmidbaur, H., J. Organomet. Chern., 1969,16,188 (synth,
nmr)
x = CI
M 675.167 Catalyst for polymn. of cyclic ethers. Purple solid. Sol.
C6H6, CH2CI2. Aida, T. et ai, Macromolecules, 1981, 14, 1166 (use) Aida, T. et ai, Makromol. Chem., 1981,182,1073; Makromol.
Chem. Rapid Commun., 1982,3, 785 (synth, use) Aida, T. et ai, J. Am. Chem. Soc., 1983, 105, 1304 (use) Yasuda, T. et ai, Macromolecules, 1983,16, 1792 (use)
C46H3~IN4 AI-10106 Ethyl(S,l 0, 1 S,lO-tetraphenyl-l 1 H,13H-porphinato(1-)
N2I,N22,N23,N24]aluminum,IOC[ Tetraphenylporphinatoaluminum ethyl
x = Et
M 668.175 Formed in situ as green soln. Inoue, S. et ai, Bull. Chem. Soc. Jpn., 1977, SO, 984 (synth)
C58H7~I:zCI6N6P6W:z AI-10107 Dichlorobis(p3-[diazenato(l-)-N:N:N']J
bis(dichloroaluminum)hexakis(dimethylphenylphosphine) bis(pyridine)ditungsten,1I0 [84836-02-2]
Cl CI PMe2Ph \ I PMe2Ph I "PMe2Ph /Al, I "PMe2Ph
CI-W N=N N-N=W-Cl
;/1 'A( 0/1 01 PMe2Ph I \ I ~ PMe2Ph ~ Cl Cl '"
M 1677.502 Red cryst. Mp 960 dec. Takahashi, T. et ai, J. Am. Chem. Soc., 1983, lOS, 1680 (synth,
ir, cryst struct)
dialuminum(4+), lIO Di-p-chlorobis[bis(methylenetriphenylphosphorane) aluminum]( 4+)
IPh3PCH2 Cl CH2PPh3]:: , / , / AI AI
/ , /, Ph3PCH2 Cl CH2PPh3
M 1230.137 (ion) Tetrachloride: [87521-44-6]. C7~6I0.hCI~4 M 1371.949 White solid (THF). Reacts with alcohols, CHCh, DMF, DMSO, H20, stable in CH2Ch at -800 • Mp 225 0 dec.
Yamamoto, Y., Bull. Chern. Soc. Jpn., 1983,56,1772 (synth, pmr)
Cl1~1O:zAI:zCIP6$$$$$ AI-10109 p-Chlorohexakis(triphenylphosphonium 'I1-methylide)
C1l4Hl02Al2Ci6P6 M 1924.583 White solid (THF). Reacts with alcohols, CHCh, CH2Ch, DMSO, H 20. Mp 231 0 dec.
Yamamoto, Y., Bull. Chem. Soc. Jpn., 1983,56, 1772 (synth)
As Arsenic CH~sCh As-10001 Methylarsonous dichloride, lOCI, 9C1
Dichloromethylarsine, 8CI. Methylarsine dichloride [593-89-5]
MeAsCh
M 160.862 Colourless liq. Mp -42.5°. Bp 132.5°.
t>CH4375000. Gibson, C.S., J. Chern. Soc., 1931,2518 (synth) Pettit, L.D. et ai, Spectrochirn. Acta, Part A, 1968, 24, 999 (ir) Svergun, V.1. et ai, Izv. Akad. Nauk SSSR, Ser. Khirn., 1970,
482; CA, 73, 9243w (nqr) Choudhury, P. et ai, Inorg. Chirn. Acta, 1978, 28, L127 (synth,
nrnr)
Bis(dimethylarsine) sulfide. Dimethylarsinothious acid anhydride [591-10-6]
M 242.042 Pesticide. Zingaro, R.A. et ai, J. Arn. Chern. Soc., 1971,93,5677 (prnr)
CSHlsAsS2Sn As-10003 (Dimetbyldithioarsinato )trimetbyItin
M 332.905 Colourless oil; stored under an atmosphere of dry
nitrogen. Dumitrescu, S.L. et ai, J. Organornet. Chern., 1984,263, 159.
CJllsAs2S~n Dimethylbis( dimethylditbioarsinato )tin
Dimethyltin bis(dimethyldithioarsinate)
As-10004
159 (cryst struct)
[Bis(trimethylsilyl)methyl]dichloroarsine [76505-21-0]
19
M 305.226 Colourless liq. BP3 94-96°. Gynane, M.l.S. et ai, J. Chern. Soc., Dalton Trans., 1980,2428
(synth, prnr, esr) Cowley, A.H. et ai, J. Chern. Soc., Chern. Cornrnun., 1983, 881
(use)
As-10006
Pale-yellow oil. Sol. CHCI3. Bpoo8 84-87°. Several relat ed compds. also prepd.
Heinicke, l. et ai, J. Organornet. Chern., 1984,258,257 (synth, prnr, crnr, uv)
As-10007 Tetracarbonyl[3-( dimethylarsino )-4,4,4-trifluoro-l-oxo-2-
(trifluoromethyl)-2-butenyl]rhenium,IICI [82113-00-6]
M 593.284 Dark-orange, air-stable cryst. (CH2Clz/hexane at -20°).
Sol. CH2CI2, CHCh. Mp 151-152°. Mihichuk, L.M. et ai, Inorg. Chern., 1982,21,3731 (synth, cryst
struct)
As-10008
C12HsAsCr2010 As-10009 Decacarbonyl[p-( ethylarsinidene )]dichromium, 110
[84133-56-2]
OC, I ~ ___ ~ I /CO OC.-Cr 'Cr-CO
OCI 'cO 06 'cO Blue-violet cryst. Struct. by analogy with As-isopropyl
deriv. Sigwarth, B. et ai, J. Organomet. Chem., 1982,235,43 (synth,
eryst struet)
[89005-46-9]
Oil. Sol. CHCI3. Bpo.ol 88-89°. Several related compds. also prepd.
Heinicke, J. et ai, J. Organomet. Chem., 1984,258,257 (synth, pmr, emr)
CI2Hl~S2 2,2',5,5'-Tetramethyl-l,1 '-bi-1H-arsole, IIC[
2,2',5,5'- Tetramethyldiarsolyl [85650-31-3]
Air-sensitive block-like yellow cryst. by subl. Mp 74-75°. Not thermochromic, unlike Sb analogue.
Ashe, A.J. et ai, Organometallics, 1983,2, 1005 (synth, cryst struct, pmr, ms, ir, raman)
C14H9AsCr20lO As-10012 (p,- tert -Butylarsinidene )decacarbonyldichromium
Decacarbonyl[!J-- [(1 ,l-dimethylethyl)arsinidene ]] dichromium, 11CI
[84133-62-0]
M 516.133 Arsenic in planar environment. Several analogues also
known. Green cryst. with metallic lustre (CH2CI2/pentane). Mp 80° dec. Ir Vco 2082w, 2026m, 2003w, 1982s, 1974s, 1948m cm- I .
Sigwarth, B. et ai, J. Organomet. Chem., 1982,235,43 (synth, ir, pmr, ms, UV, cryst struct)
20
yl)( dimethylphenylarsine )molybdenum, 110 [88545-42-0]
M 625.760 Light-sensitive, air-stable cryst. Sol. CH2Ch. Salem, G. et ai, J. Chem. Soc., Dalton Trans., 1983,2117
(synth)
2,4-Diphenylarsabenzene [ 63466-40-0]
M 292.211 Bp 140-150°. Markl, G. et ai, Angew. Chem., 1972,84,440.
As-10014
C17H 13As 2,6-Diphenylarsenin,1I0
As-1001S
Markl, G. et ai, Tetrahedron Lett., 1983,24,4079 (synth, pmr, ms)
C2oH20As2 1,2-Phenylenebis[ methylpbenylarsine], IOC[
(R,R)-form
As-10016
Yellow syrup. BpO.05 180-185°. May be resolved via optically active Pd-complex.
(R*,R*)-form [57375-33-4] (+ )-form Large friable rods. Mp 75-76°. [0']589+95° (c, 0.88 in
CH2Cl2).
(S*,S*)-form [57341-01-2] (- )-form Mp 75-76°. [0']589-95.2° (c, 0.88 in CH 2Ch).
(RS,SR)-form [55289-91-3] meso-form White leaflets (MeOH). Mp 61-62°.
(RR,SSj-form [55289-90-2] (±)-form Mp 88-88.5°. Henrick, K. et ai, Aust. J. Chern., 1974,27,727.
Henrick, K. et ai, J. Chern. Soc., Dalton Trans., 1975, 1506 (synth)
Roberts, N .K. et ai, J. Chern. Soc., Dalton Trans., 1979, 2015 (resoln)
Roberts, N.K. et ai, lnorg. Chern., 1981,20,1892.
C2oH21AsGeS2 As-10017 (Dimethyldithioarsinato )triphenylgermane
[(Dimethylarsinothioyl)thio] triphenylgermane, / /CI. Tri phenylgermyl dimethyldithioarsinate [89901-33-7]
M 473.018 White, moisture-sensitive solid. Mp 105°. Silaghi-Dumitrescu, L. et ai, J. Organornet. Chern., 1983,259,
65.
Triphenylplumbyl dimethyldithioarsinate. Triphenyl lead dimethyldithioarsinate
Ph3PbS2AsMe2
M 607.628 White solid. Mp 195°. Silaghi-Dumitrescu, L. et ai, J. Organornet. Chern., 1983,259,
65.
[87016-06-6]
M613.003
As-10019
First example of a stable diarsene. Orange cryst. (MeOH). Mp 86-88° dec.
Sulfur cycloadduct: [87016-07-7]. Bis[ tris( trimethylsilyl)meth yl] thiadiarsirane, / /CI. Bis[tris(trimethylsilyl)methyl]diarsathiiran. CzoH54AszSSi6 M 645.063 Cryst. Mp 158-162°.
Couret, C. et ai, Tetrahedron Lett., 1983, 24, 2769 (synth, prnr, UV, rns)
C22H 29As As-10020 2-Diphenylarsino-l-isopropyl-4-methylcyclohexane
M 368.393 (1S,2R,4R)-lorm [83845-72-1]
Diphenylmenthylarsine. (- )-form Cryst. Mp 52-53°. [a]D -79.6° (c, 1.47 in CH2CIz). PhCH2Br adduct: Benzyldiphenylmenthylarsonium
bromide. Cz9HMAsBr M 539.429 Cryst. (EtOH/Et20). Mp 188-190°. [a]D +2.5° (c, 2.0 in CH2Cl2).
21
(1S,2S,4R)-lorm [83845-71-0] Diphenylneomethylarsine. (+ )-form White needles (MeOH). Mp 146-148°. [aJo +69.6° (c,
0.4 in CH2CI2). Allen, D.G. et ai, Organornetallics, 1983,2,394 (synth, prnr)
C23H17As 2,4,6-Triphenylarsenin, IlCI
As-10021
C23H2oAsINi As-10022 (1/5-2,4-Cyclopentadien-l-yl)iodo( triphenylarsine )nickel, lOCI,
9CI
[ 1298-78-8]
M 556.927 Cryst. Kuhn, N. et ai, J. Organornet. Chern., 1984, 269, C47 (synth,
prnr)
Mod. sol. CH2CI2•
Kreissl, F.R. et ai, Organornetallics, 1983, 2, 1266 (synth, ir, nrnr, props)
C24H20AsP Diphenyl(diphenylarsino)phosphine,lIel
As-10024
Disproportionates. Formed as equil. mixt. with Ph2PPPh2 and·Ph2AsAsPh2 in soln.
Belforte, A. et ai, lnorg. Chern., 1984, 23, 1504 (synth, nrnr, bibl)
CuHzoAsz As-1002S 1,2,3,4-Tetraphenyl-l,2-diarsetene
By reaction of Hexaphenylhexarsenane. As-I 0030 with Ph2C2. Cryst. Mp 122°. Reacts with Fe3(CO)12 to give Hexacarbonyl[w [( 1.2-diphenyl-I.2-ethendiyl) bis(phenylarsinidene) ]-As .As' :As .As'] diiron. As-I 0028
Sennyey, G. et ai, Organometallics, 1983,2,298 (synth, cryst struct, cmr, ms)
Cz,"z~sFeOz As-10026 Acetylcarbonyl( T/5-2,4-cyclopentadien-l-yl)(triphenylarsine)
M 498.235 Red-brown cryst. (hexane/MeOH). Dec. in CHCb. Mp
127-128°. Gingell, A.C. et ai, J. Organomet. Chem., 1975,99, C27 (synth,
ir, pmr)
As-10027
Ennen, J. et 01, Angew. Chem., Int. Ed. Engl., 1981,93, 117 (synth, pmr, ms)
C3zHzoAszFez06 As-10028 Hexacarbony I[po-[ (1 ,2-di pheny 1-1.2-ethenediy 1)
Bis(phenylarsinidene)]-As, As' :As,As' ]Diiron, 11 CI
[83815-89-8]
Ph Ph F\
Ph-As As-Ph IXI
OC-Fe-Fe-CO /' I 1"-
Sennyey, G. et 01, Organometallies, 1983,2,298 (synth, emr, ir, ms)
22
C3zHzsAs3 As-10029 1,2,3,4,5-Pentaphenyl-l,2,3-triarsolene
2.3-Dihydro-l.2.3.4.5-pentaphenyl-lH-l.2.3-triarsole. IICf [83801-87-0]
M 634.314 Mp 126°. Sennyey, G. et ai, Organometallics, 1983,2,298 (synth, emr,
ms)
Ph/ 'A'( 'Ph I Ph
Chair conformn. in AS6 ring. Growth inhibitor of mammalian cells; olefin polymerisation catalyst. Colourless cryst. Mp 210-211 ° dec. Forms a yellow polymer on melting.
Lyon, D.R. et aI, J. Chem. Soc., 1945,30 (synth) Wittig, G. et aI, Justus Liebigs Ann. Chem., 1952,577, I. Anschiitz, L. et aI, Naturwissenschaften, 1956,43,59 (synth) Kraft, M.Ya. et aI, Dokl. Akad. Nauk SSSR, Ser. Sci. Khim.,
1960,131,1074 (synth) Sarchuk, W.B. et aI, Proe. Soc. Exptl. BioI. Med., 1960, lOS,
543 (use) Donohue, J., Acta Crystallogr., 1962, 15,708 (struet) B.P., 1 000348, (/965); CA, 64,2191 (use) Rheingo1d, A.L. et 01, Organometallics, 1983,2,327 (eryst
struct)
CA. Ai) As As
/ I I "- Ph ~ Ph
M 776.430 Air-stable cryst. (pet. ether). Mp 106.5°. Ennen, J. et aI, Angew. Chem., Int. Ed. Engl., 1981,93, 117
(synth, pmr, ms)
C38HJOAS2Ir02e Dicarbonylbis(triphenylarsine)iridium(l +), 9CI
OC L
L = AsPh3
M 860.717 (ion) Chloride: [41782-33-6]. C38H~szClIrOz M 896.170 Yellow solid (Me2CO/pet. ether). Sol. CHCb, Me2CO, MeN02. Mp 169-173° dec.lr Peo 2020 cm- I
(nujol). Herde, J.L. el ai, Can. J. Chem., 1973,51, 1016 (synlh, ir)
C43H39As3C002e As-10033 Dicarbonyl[[2-[( diphenylarsino )methylJ-2-methyl-l,3-
propanediyl]bis[ diphenylarsine ]-As,As' ,As "]cobalt(l + ), 9CI Dicarbonyl[1,1 ,1-tris(diphenylarsinomethyl)ethane] cobalt( 1 + ). [[ 2,2-Bis [( diphenylarsino )methyl]propyl] diphenylarsine ]dicarbonylcobalt( 1 +)
M 871.478 (ion) Tetraphenylborate: [54003-39-3].
C67Hs.,As3BCoOz M 1190.710 Red-orange cryst. (CH2Ch/dibutyl ether). Ir Peo 2020, 1972 cm- I (CH2CI2).
Dapporto, P. el ai, [norg. Chem., 1975, 14,1643 (symh, ir, uv)
C","3IAs309R~ As-10034 Tri-I'-carbonylhexacarbonyI[p3-[ methylidynetris[diphenylar
sineJ-As:As':As"]]tetrarhodium,1I0 Nonacarbonyl[1,1,1-tris(diphenylarsino)methane] tetrarhodium [82246-61-5]
CO OC ....... ' /CO
PhzQ"-...... i----QPhz Q = As C'H
M 1364.132 Deep-purple cryst. (THF /hexane). Insol. hexane, sol.
CH2Ch, THF. Ir Peo 2065m, 2055sh, 2015s, 1990m, 1848w, 1805m cm- I (CH2Ch).
Bahsoun, A.A. el ai, Organomelal/ics, 1982, 1,1114 (symh, ir, cmr, P-31 nmr)
23
diphenylphosphine-As:P]]dirhodium(l +), 110 Dicarbonyl-p.-chlorobis [p.- [(diphenylarsino )(diphenylphosphino )methane]] dirhodium(1 +)
Ph Ph \~/
Ph-P As-Ph
Ph Ph
head-tail-/orm
M 1153.973 (ion) Exists as a mixt. of head-tail (as shown) and head-head
isomers. Head-tail-form
CszH44AszCIF60zP3Rhz M 1298.937 Orange solid. Sol. CH2Ch, Me2CO. Ir Peo 1981,1965 cm- I (nujol).
Dicarbonyldichlororhodate( 1-): C54H~szCh04PzRh3 M 1383.805 No phys. props. reported.
Guimeraus, R.R. el ai, [norg. Chim. Acta, 1983,77, LI77 (P-31 nmr)
Enlow, P.O. et ai, Organometallics, 1983,2,64 (symh, ir, UV, P- 31 nmr)
CS2H~S2Ch02P2Rb2 As-10036 Dicarbonyldichlorobis[,,-[[(diphenylarsino)methylJ
diphenylphosphine-As:P]]dirhodium, 110 Dicarbonyldichlorobis[p.- [(diphenylarsino ) (diphenylphosphino )methane]] dirhodium. Bis [carbonylchloro[p. [(diphenylarsino )(diphenylphosphino )methane]] rhodium] [83153-27-9]
M 1189.426 Exists as a mixt. of head-tail (as shown) and head-head
isomers. Orange solid. Ir Peo 1967 cm- I (KBr). Head-tail-form [83153-27-9]
Major form. Head-head-form [89144-46-7]
Minor form. Guimeraus, R.R. et ai, [norg. Chim. Acta, 1983, 77, L 177 (P-3 I
nmr) Enlow, P.O. et ai, Organometallics, 1983,2,64 (symh, ir, UV,
cmr, P-31 nmr, props)
CsJll.uAs4ClIr203 $ As-10037 I'-Carbonyldicarbonyl-I'-chlorobis(p-[ methylenebis[ dipheny
Ph /'.... Ph \ ............... I
Ph-Q 0 Q-Ph
M 1448.508 (ion) Tetraphenylborate: [74978-00-0]. C77H~s4BClIr203 M 1767.740 Orange cryst. (CH2Ch/Et20). Sol. CH2Ch. Mp 1840
dec. Ir Peo 1974, 1950, 1816 cm-1 (nujol). Mague, J.T. et ai, Inorg. Chern., 1980, 19, 3743 (synth, ir, crnr)
CS3H4..As4C103Rh2$ As-10038 I'-Carbonyldicarbonyl-I'-chlorobis[I'-[methylenebis[dipheny
larsine]-As:As']dirhodium( 1 +), lOCI Bis[/l-bis(diphenylarsino )methane] -/l-carbonyldicar bonyl-wchlorodirhodium(J +)
Ph " Ph \ ............... I
Ph Ph
M 1269.879 (ion) Readily loses CO in soln. Tetraphenylborate: [70561-95-4].
C77H64As4BCI03Rh2 M 1589.111 Buff-orange cryst. (THF /Et20 under CO atm.). Sol. CH2Ch, in sol. Et20. Mp 1680 dec. Ir Peo 1991,1975, 1864 cm- 1 (nujol).
Mague, J.T. et ai, Inorg. Chern., 1979, 18, 2060; 1980, 19, 3743 (synth, ir, crnr, UV)
As-10039 1,5,9,13,17,21-Hexaarsa-l,5,9,13,17,21,-hexaphenyltetra
cosane, lOCI
Ph--As As--Ph
~AS A~ Ph V Ph
M 1164.645 Formed as mixt. of stereoisomers. Air-stable oil. Ennen, J. et ai, Angew. Chern., Int. Ed. Engl., 1981,93, 118
(synth)
24
diphenylphosphine-As:P]]bis(2-isocyano-2- methylpropane)dirhodium(l +), 110 Carbonylchlorobis[}L- [( diphenylarsino) (diphenylphosphino )met hane] bis [tert butyl isocyanide ]dirhodium( 1 +)
Ph Ph \~I
Cl""" I RNC"""I Ph-A~ JP-Ph
I '-...../ \ Ph Ph
R = -C(CH3h M 1292.228 (ion) Probably exists as a mixt. of head-tail (as shown) and
head-head isomers. Hexaj7.uorophosphate: [83174-74-7].
C61H62As2CIF6N20P3Rh2 M 1437.192 Burgundy cryst. Unstable in CH2Ch. Ir PeN 2120, Peo 1954 cm- 1 (nujol).
Enlow, P.O. et ai, Organornetallics, 1983, 2, 64 (synth, ir, UV)
C7sHssAs2N4P2Rh2$$ As-10041 Bis[/l-[[( diphenylarsino )methyl]diphenylphosphine-As:P]]
tetrakis(isocyanocycIohexane)dirhodium(2+),l1Q Bis[/l- [( diphenylarsino )(diphenylphosphino )methane]] tetrakis( cyclohexyl isocyanide )dirhodium( 2+). Bis [/l [(diphenylarsino) (diphenylphosphino )methane] bis(cyclohexyl isocyanide )rhodium] (2+)
Ph Ph \/'.....I
RNC"""IRNC"""I Ph-As P-Ph
1'-...../\ Ph Ph
R=-Q M 1499.182 (ion) Exists as a mixt. of head-tail (as shown) and head-head
isomers. Head-tail-form
Head-head-form
Minor form. No phys. props. available. Enlow, P.O. et ai, Organometallics, 1983,2,64 (synth, ir, UV, P-
31 nrnr)
[15278-97-4]
Au-10001
Fine white needles. Sol. CH2Ch, Me2CO. Mp 231-233° (226-228 0). Light -sensitive.
Duddell, D.A. et ai, J. Chern. Soc. (A), 1970,545 (synth, ir, ra man)
Bruce, M.1. et ai, Aust. J. Chern., 1984,37, 1163 (synth)
CsH1..AuP Au-10002 Methyl(trimethylphosphonium 1/-methylide)gold, 9C[
[55804-42-7]
MeAuCH2PMe3
M 302.106 Colourless cryst. Sol. Et20, C6H6, toluene. Mp 119-121 °
dec. 31p nmr 023 ppm (rei H3P04). Ir VAu.C 597, 538, 518 cm-I.
Schmidbaur, H. et ai, Chern. Ber., 1975, 108, 1321 (synth, ir, nrnr)
Inorg. Synth., 1978, 18, 141 (synth, ir, nrnr)
CJIlsAuBr3P Au-10003 Tribromo( triethylphosphine )gold, IIC[
[56213-25-3]
M 554.837 Red-orange prisms. Sol. toluene, EtOH. Mp 129-131 °
(129°). Mann, F.G. et ai, J. Chern. Soc., 1940, 1235 (synth) Eggleston, D.S. et ai, Acta Crystallogr., Sect. C, 1984,40, 1357
(cryst struct)
[33012-33-8]
Au-10004
Colourless cryst. or oil. Sol. Et20, C6H6. Mp 23°. Subl. at r.t./0.004 mm.
Coates, G.E. et ai, J. Chern. Soc., 1963,421 (synth, ir) Shiotani, A. et ai, J. Am. Chern. Soc., 1971,93,1555 (synth,
nrnr) Tamaki, A. et ai, J. Chern. Soc., Dalton Trans., 1973,2620
(synth) Stein, J. et ai, J. Am. Chern. Soc., 1981, 103,2192 (nrnr, pel
CsHsAu Phenylethynylgold, IOC[
Gold phenylacetylide [34679-27-1]
M 298.094 Polymeric. Forms adducts with PR3. Yellow powder. Mp
162-164° (150°). Ir Vc==c 1973 cm-I. Light-sensitive, rapidly turning green.
Isopropylamine adduct: CllH l 0.uN M 357.205 White needles. Sol. Me2CO. Ir VC==C 2122 cm-I. Darkens> 115 0.
PEt3 adduct: C14H20AUP M 416.252 Colourless cryst. Sol. C6H6. Mp 83-85°.
PPh3 adduct: [87960-48-3]. C26H 20AuP M 560.384 Useful alkylating agent for Hg(II) and Pt(II) compds. Pale-cream plates (hexane/C6H6/CH2Ch). Sol. CH2Ch, C6H6. Mp 135-138°.
Calvin, G. et ai, Chern. Ind. (London), 1959, 1628 (synth) Coates, G.E. et ai, J. Chern. Soc., 1962,3220 (synth) Nast, R. et ai, Z. Anorg. Allg. Chern., 1964,330, 311 (synth, ir) Calvin, G. et ai, Acta Crystallogr., 1967,23, 156 (cryst strucr) Bruce, M.1. et ai, Aust. J. Chern., 1984,37, 1163 (synth) Cross, R.J. et ai, J. Organornet. Chern., 1984,265, C37 (deriv)
CsHzoAuzBrz Di-wbromotetraethyldigold, IOC[
Au-10006
Colourless needles. Sol. C6H6, pet. ether, CHCI3, Et20. Mp 58° dec. Odour resembles bromocamphor.
I>Can dec. violently when v. dry; explodes on heating to 70°
Monomer: [26645-10-3]. Bromodiethylgold. C4H lOAuBr M 334.994 Unknown.
Pope, W.J. et ai, J. Chern. Soc., 1907, 2061 (synth) Buraway, A. et ai, J. Chern. Soc., 1937, 1690 (cryst struct) Armer, B. et ai, Angew. Chern., Int. Ed. Engl., 1970,9,101. Kuch, P.L. et ai, J. Organornet. Chern., 1976, 122,429 (haz)
CsHzoAuzClz Au-10007 Di-Il-chlorotetraethyldigold As Di-wbromotetraethyldigold, Au-10006 with
X=CI
M 581.085 White cryst. Sol. C6H6, CHCI3, py. Mp 48° dec. Light
sensitive. Monomer: Chlorodiethylgold.
C4H lOAuCI M 290.543
Unknown. Kharasch, M.S. et 01, J. Am. Chem. Soc., 1931,53,2701 (synth) Armer, B. et 01, Angew. Chem., Int. Ed. Engl., 1970,9,101.
C9HuAuBrlN Au-10008 Dibromo(2-[(dimethylamino)methyIJphenyl-C,NJgold,llo
X = Br
Yellow cryst. (CH2Ch/Et20). Mp 172° dec. Vicente, 1. et 01, J. Organomel. Chem., 1984,268,191 (synth)
C9H u AuCIzN Au-10009 Dichloro[2-[(dimethylamino)methyIJphenyl-C,N]gold,llo
[91946-52-0J As Dibromo[2-[(dimethylamino)methyIJphenyl-C,N]
X=CI
M 402.073 White cryst. Mp 185° dec. Vicente, 1. et 01, J. Organomel. Chem., 1984,268, 191 (synth)
C9H u AuI1N Au-10010 [2-[(Dimethylamino)methyIJphenyl-C,N]diiodogold,IICI
[91946-54-2J As Dibromo[2- [( dimethyl amino )methylJ phenyl-C,N]
gold, Au-l 0008 with
X = I M 584.976 Red solid. Mp 105° dec. Vicente, 1. el 01, J. Organomet. Chern., 1984,268,191 (synth)
ClOHuAuNO Au-10011 [Ethoxy[( 4-methylphenyl)imino JmethylJgold
[Ethoxy(p-tolylimino )methyl-C,NJgold
Etc! b ~ J
26
Au-10008 - Au-10015
C30H~U3N303 M 1077.532 Colourless needles. Sol. CHCI3• Mp 181-183° dec.
Tiripicchio, A. et 01, J. Organornet. Chern., 1979, 171,399 (synth, cryst struct)
Cu H 19AuCIzS Au-10012 Dichloro(phenyl)( dipropyl sulfide )gold
Dichlorophenyl[l ,l-thiobis[propane))gold, 9CI [35798-02-8)
M 463.215 cis-form
V. pale-yellow solid. Mp 113-114°. Air-stable. Liddle, K.S. et 01, J. Chern. Soc., Chern. Comrnun., 1972, 26
(synth, ir) McPartlin, M. et 01, J. Organornet. Chern., 1973,57, C25 (cryst
struct)
no [91946-55-3) As Dibromo[2- [( dimethylamino )methyl) phenyl-C,N]
gold, Au-10008 with
X=OAe
M 449.256 White solid. Mp 135° dec. Vicente, 1. et 01, J. Organornet. Chern., 1984, 268, 191 (synth)
C14Hl~UP Au-10014 (Cyclopentadienyl)triisopropylphosphinegold
2,4-Cyclopentadien-l-yl[ tris(J -methylethyl)phosphine J gold,llCI [89989-57-1)
M 422.300 Colourless eryst. Sol. C6H 6. Mp 1050. Air-sensitive. 31p
nmr 63.8 ppm (reI. 85% H 3P04).
Werner, H., J. Organornet. Chern., 1984,262,123 (synth, cryst strucl, crnr, nrnr)
ClJiloAuCr206e Au-10015 Bis[ (.,,5-2,4-cyclopentadien-l-yl)tricarbonylchromate J
aurate(l-) Auratehexacarbonylbis( 7/5 -2,4 -cyclopentadien-l-yl) dichromate(J -), lICI
[@=ir{CO Au-J~~le CO OC CO
M 599.210 (ion) Tetrabutylammonium salt: [76796-11-7). C3zH~uCrzN06 M 841.677 Light yellow-green eryst. Sol. THF, CH2Ch. M p 1240. Ir Vco 1926,1905,1826 em-I (THF); 1919, 1890, 1825, 1795 em-I (KBr); VAuCr 194 em-I. Best stored in dark, under N2 at low temps.
Braunstein, P. et ai, Inorg. Chern., 1984,23,4057 (synth, cryst struct, ir)
C2oH17AuNP Au-10016 Cyano(metbylenetripbenylpbospborane)gold
M 499.301 Undergoes oxidative addition reactions with halogens.
Au-C bond not cleaved with dry HCI. Sl. violet colouration. Sol. CHCI3, THF. Mp 185-188°. Air stable.
Bowmaker, G .A. et ai, J. Chern. Soc., Dalton Trans., 1984, 2859 (synth, nrnr, ir, rarnan)
C2oH tsAu02P (Acetato-O)(tripbenylpbospbine)gold,lIcl
Triphenylphosphinegold acetate [24169-88-8]
Colourless prismatic cryst. Sol. CH2Ch, CHCI3, Me2CO. Mp 185-186°.
Nichols, 0.1. et ai, J. Chern. Soc. (A), 1969, 2581 (synth, ir, prnr)
Jones, P.G., Acta Crystallogr., Sect. C, 1984,40, 1320 (cryst struct)
Au-10018 Auranofin, BAN
M 678.483
rO~AuPEt3
AcO~ OAc
Antirheumatic drug. Mp 110-111 0. [am -55.3° (c, 1.0 in MeOH).
t> MD6500000. Sutton, B.M. et ai, J. Med. Chern., 1972,15,1095 (synth,
pharrnacol, tox

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Dictionary of Organometallic Compounds: First Supplement

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