Appendix

This appendix is a brief review of recent literature, and covers ap­proximately eight months (the last half of 1967 and the first two months of 1968). The large number of additional references compiled over so short a period of time reflects the amount of work currently conducted in this area.

A. CARBONIMIDOYL DIHALIDES

The direct chlorination of chlorosulfonyl isocyanate (I) to chloro­sulfonylcarbonimidoyl dichloride (II) by means of phosphorus penta­chloride has been reported (42). However, severe conditions are required and the yield is low. Selective fluorination of II with antimony trifluoride produces the sulfonyl fluoride III (42).

ClS02 NCO + PCls --+ ClS02 N=CCI2 + SbF 3 --+ II

In a recent publication by HoItschmidt and his co-workers the mechan­ism of the high-temperature chlorination of N-methylpyrrolidone was discussed (43). In this reaction 1-chlorocarbonylhexachloropropyl-3-car­bonimidoyl dichloride is formed as a major product (see Chapter 2). Further work related to the nucleophilic substitution reactions of carbonimidoyl dichlorides with water (48), hydrogen sulfide (48), alcohols e1 ), mercaptans e1 ), and amines e1 ) has been reported, and a step-wise displacement of the chloro groups was demonstrated by Neidlein and his students e1,32).

For example, reaction of arenesulfonylcarbonimidoyl dichlorides IV with methyl mercaptan yields the 1-chlorothioformimidates V, which, upon further reaction with primary and secondary amines, yield the S,N-acetals VI e1 ).

211

212

RS02 N=CCI2 + CH3SH IV

RS02 N=C-SCH3 + RzNH I

CI

Appendix

-----. RS02 N=C-SCH3 I

CI V

-----. RS02 N=C-SCH3 I NRz VI

With 1,2-diols and dithiols the corresponding cyclic acetals are ob­tained e 1). Likewise, aminoalcohols, aminothiols, and diamines yield cyclic acetals upon reaction with acyl carbonimidoyl dichlorides (6). The reaction of IV with acylhydrazides produces N-sulfonylamino-l,3,4-oxadiazoles VII eO).

N-N

RS02 N=CCI2 + R'CONHNH2 -----. RS02 NH JlOJlR, VII

The reaction of amide OXlmes with carbonimidoyl dichlorides has been reported as well e 3).

Several recent articles are concerned with the synthesis and reactions of perfluorinated carbonimidoyl difluorides. Glemser and his students e) reported the formation of trifluoromethylcarbonimidoyl difluoride in the reaction of cyanogen chloride and nitrogen trifluoride at 450-500°C. Further work related to the chemistry of perfluoro-bis-carbonimidoyl difluorides has been presented by Ogden and Mitsch e5- 37 ). For example, photolysis of difluoromethane-l,l-bis-carbonimidoyl difluoride (VIII) generates the in­teresting radical species CF2 =N·, which can be trapped by a variety of radical, carbene, and olefin substrates e5 ). In the presence of fluoride ion VIII rearranges to bis(trifluoromethyl)carbodiimide (IX) e6 ). Hydrolysis of VIII yields 1,3-bis (trifluoromethyl)urea (X) e7 ).

F 2C=N-CF2-N=CF2 VIII ~o

F 3CN=C=NCF3 IX

F 3CNHCONHCF 3 X

Appendix 213

B. IMIDOYL HALIDES

A novel method of synthesis of imidoyl chlorides has been reported by Kresze and Wucherpfennig e3 ). The authors treated N-sulfinylsulfonamides XI with aliphatic and aromatic carboxylic acid chlorides and obtained N-arenesulfonylimidoyl chlorides XII in excellent yield.

RSOzN=S=O + R'COCI XI

------. RSOzN=CR' + SOz I

CI XII

The formation of imidoyl bromides (XIII) in the reaction of 2-bromo­acetophenone oxime (XIV) with triphenylphosphorus has been reported by Masaki et al. eS ).

C6H sC-CHzBr + P(C6HSh II

------. C6HSN=C-CH3 + OP(C6HSh I

NOH Br XIV XIII

Imidoyl bromides are also obtained when oximes are treated with the phosphonium salt XV. For example, reaction of XV with the oxime XVI produces the imidoyl bromide XVII, which can be dehydrohalogenated to the ketenimine XVIII by means of triethylamine eS ).

$ C6Hs-C-CHzC6Hs + BrP(C6H shBr8

II NOH XV

XVI XVII

C6HSN=C=CHC6HS XVIII

The significance of imidoyl halides as intermediates in the Beckmann rearrangement has been pointed out earlier (see Chapter 3). In the Chapmann rearrangement imidoyl chlorides are used to prepare imidates, which under­go rearrangement to yield N-aroyl derivatives of diarylamines (4). For example, reaction of the sodium salt of dimethyl 4,6-dihydroxyisophthalate (XIX) with the benzimidoyl chloride XX yields the bis-imidate XXI, which can be thermally rearranged and hydrolyzed to produce the diamines XXII (4).

214

CH300CYpCOOCH3

NaO~ONa XIX

XXII

+ 2 RN=C-C6Hs I CI xx

Appendix

This reaction is quite useful to convert an aryl hydroxy compound to the corresponding amino derivative.

The hexachloroantimonate salts of unsubstituted imidoyl halides have been converted to the corresponding azides (44). Boron trichloride com­plexes of N-substituted benzimidoyl chlorides are reported by Hall and co-workers e4 ).

Two recent review articles related to the Viis meier-Haack reaction have appeared (17,34), and the formylation of 4H-quinolizine-4-ones by means of the DMF-POCl3 complex has been reported (47).

The reaction of chlorodimethylformiminium chloride (XXII) with diazoketones and ethyl diazoacetate gives rise to the formation of IX-diazo­aldehydes XXIII (46). In contrast, diazomethane undergoes reaction with XXII to yield 2-dimethylamino-l,3-dichloropropane (46).

EB RCOCH 2 N 2 + (CH 3 hN:.!..!CHCI]CI8 ---+

XXII

lH,o OCHCN2 COR

XXIII

Appendix 215

The formylation of polyene aldehydes e3 ) and a,{3-unsubstituted ketones e4 )

with the Vilsmeier reagent (DMF-POCl3) has been reported recently. For example, reaction of the ketones XXIV with the Vilsmeier reagent produces the iminium salts XXV, which are hydrolyzed to the aldehydes XXVI. The latter compounds form the conjugated ene-yne derivatives XXVII upon addition of their dioxane solution to dilute sodium hydroxide at 80--90°C e4 ).

RCH=CHCOCH3 XXIV

DMF-POC\ EB RCH=CH -C=CHCH'--'--'N(CH3hJCl8

I Cl XXV

lH 20

RCH=CH-C CH XXVII

~ RCH=CH-C=CH-CHO I

Cl R = Aryl

XXVI

Arylchloroformates XXVIII react with dimethylformamide to liberate carbon dioxide and form the iminium salts XXIX. Solvolysis of XXIX with methanol produces the corresponding phenol, N,N-dimethylformamide and methyl chloride (41).

C6 H sO-C-Cl + (CH3hNCHO

" EB

--+ C6 HsOCH'--'--'N(CH3hJCl8

o XXIX

XXVIII

C6 H sOH + CH3Cl + (CH 3 hNCHO

The reaction of sulfur dichloride with N,N-dimethylformamide and thioformamide has been investigated by Hasserodt e6 ).

C. HALOFORMAMIDINES

The reaction of N-acylthioureas XXX with carbonyl chloride yields the chloroformamidines XXXI, which are readily dehydrochlorinated to N-acylcarbodiimides XXXII e9 ).

RCONHCSNHR' + COCl2

xxx --+ RCON=C-NHR'

I XXXI Cl

l-HCl RCON=C=NR'

XXXII

216 Appendix

N-Acetylchloroformamidines XXXIII undergo reaction with methylene­bis-thioamides XXXIV to produce mixtures of 4H-l,3,5-thiadiazines XXXV and N-acylthioureas XXXVI e S).

RN=C-N(COCH3)R + R'CNHCH2NHCR' I II II o s s

XXXIII XXXIV XXXV

+ RNH -C-N(COCH3)R II s XXXVI

The synthesis of N-(chlorofluorophosphonyl)-N' -arylchloroformamidines has been reported by Derkach and Narbut (9).

Reaction of chloroformamidinium chloride (XXXVII) (cyanamide dihydrochloride) with diethyl iminocarbonate yields diethyl N-cyano­imidocarbonate (XXXVIII) (1).

EB H2N-:'':':C':'::NH2JOe + (C2H sOhC=NH -----+

I CI

XXXVII (C2H sOhC=NCN + NH4 CI XXXVIII

Chloroformamidinium chloride also undergoes rapid reaction with (SbCI4 N 3h to produce the azide XXXIX (4S).

$ -----+ 2 H2N -C-NH2JCle

I N3

XXXIX

The synthesis of perfiuorinated fluoroformamidines has been reported by Koshar and co-workers e2 ).

D. HALOFORMIMIDATES AND HALOTHIOFORMIMIDATES

The reaction of aryl cyanates with hydrogen chloride or hydrogen bromide in an inert solvent produces the haloformimidinium halides XL e6 ).

ROCN + HX

x = CI.Br

Appendix 217

In a similar manner antimony pentachloride and aluminum trichloride form 1: 1 adducts with aryl cyanates CZ7).

A comprehensive article related to the formation of aryl-l-(chloro­thio)formimidoyl chlorides XLI appeared recently (40), and the reaction of XLI with a variety ofamines has been reported eS ). The enormous reactivity of XLI was further evidenced by the formation of 1 : 1 adducts with alde­hydes and vinyl ethers e9 ). For example, reaction of XLI (R = C6 H 5 ) with vinylethyl ether yields 3-phenyl-l,3-thiazolin-2-one (XLII) e9 ).

RN=C-SCl + CH 2 =CH-OC2 H 5

I CI

XLI

E. HYDRAZIDOYL HALIDES

-Hel --.

Further work related to the cyclization of the nitrile imides, generated from N-o-nitroarylhydrazidoyl bromides, has appeared CZ), and the reaction of hydrazidoyl halides with azide ion e 9) and phenylhydrazine eS) has been studied. Lozinskii et al. CZ5) have shown that chlorooxalylarylhydrazidoyl chlorides (see Chapter 7) react with azide ion preferentially on the halo group attached to the carbonyl group.

Dehydrohalogenation of hydrazidoyl halides in the presence of furan gave rise to the formation of the 1,3-cycloadducts XLIII of furan and the corresponding nitrile imides (S).

RC=NNHR' -HBr, RC-N~NR' + I

Br o °

F. CYCLIC IMIDOYL HALIDES

/0"11 R-'-~-------,'"I J I

'N/ I R' XLIII

Further work related to the reaction of succinonitrile and glutaro­nitrile and some of its derivatives with hydrogen halide has been reported and the cyclic amidinium structures XLIV and XL V were verified by NMR studies eO,!!).

218 Appendix

~L~lNH,lxe ~¥NH,lxe XLIV XLV

The nucleophilic substitution reactions of 3-chloro-l,2-benzisoxazole (XLVI) have been investigated by B6shagen (5), and the author noted that cyclic benzhydroxamoyl chlorides, such as XL VI, react more slowly than the open-chain derivatives.

()-? ~N

CI XLVI

+ :B ----+

B = OH-, OR-, R 2N-, N,

Kinetic investigations related to nucleophilic substitution reactions of halo­quinolines have been reported recently (,12,20,21) and again the increased reactivity of the halo group adjacent to the ring nitrogen was verified.

REFERENCES

I. Allenstein, E., and Fuchs, R., Chern. Ber. 100,2604 (1967). 2. Barnish, I. T., and Gibson, M. S., J. Chern. Soc. (C), 8 (1968). 3. Biermann, U., Glemser, 0., and Knaak, J., Chern. Ber. 100,3789 (1967). 4. Bock, G., Chern. Ber. 100,2870 (1967). 5. Boshagen, H., Chern. Ber. 100,3326 (1967). 6. Burkhardt, J., and Hamann, K., Chern. Ber. 100,2569 (1967). 7. Calligaris, M., Illuminati, G., and Manno, G., J. Arn. Chern. Soc. 89, 3518 (1967). 8. Caramella, P., Tetrahedron Letters 743 (1968). 9. Derkach, G. I., and Narbut, A. V., Zh. Obshch. Khirn. 37, 1364 (1967); Chern. Abstr.

67, 10840 (1967). 10. Duquette, L. G., and Johnson, F., Tetrahedron 23,4517 (1967). II. Duquette, L. G., and Johnson, F., Tetrahedron 23, 4539 (1967). 12. Gene!, F., Illuminati, G., and Marino, G., J. Arn. Chern. Soc. 89, 3516 (1967). 13. Grundmann, C., and Richter, R., Tetrahedron Letters 963 (1968). 14. Hall, D., Ummat, P. K., and Wade, K., J. Chern. Soc. (A), 1612 (1967). 15. Hartke, K., Arch. Pharrn. 300, 766 (1967). 16. Hasserodt, U., Chern. Ber. 101, 113 (1968). 17. Hazebroucq, G., Ann. Pharrn. Franc. 24, 793 (1966); Chern. Abstr. 67,10854 (1967). 18. Hegarty, A. F., and Scott, F. L., J. Chern. Soc. (C), 2507 (1967). 19. Hegarty, A. F., Aylward, J. B., and Scott, F. L., J. Chern. Soc. (C), 2587 (1967).

Appendix 219

20. Illuminati, G., Marino, G., and Sieiter, G., J. Arn. Chern. Soc. 89, 3510 (1967). 21. Illuminati, G., Linda, P., and Marino, G., J. Arn. Chern. Soc. 89, 3521 (1967). 22. Koshar, R. J., Husted, D. R., and Wright, C. D., J. Org. Chern. 32, 3859 (1967). 23. Kresze, G., and Wucherpfennig, W., Chern. Ber. 101,365 (1968). 24. Lotzbeyer, J., and Bodendorf, K., Chern. Ber. 100, 2620 (1967). 25. Lozinskii, M. D., Kukota, S. N., and Pel'kis, P. S., Probl. Poluch. Poluprod. Prorn. Organ.

Sin., Akad. Nauk SSSR 193 (1967); Chern. Abstr. 68,12957 (1968). 26. Martin, D., and Weise, A., Chern. Ber. 100, 3736 (1967). 27. Martin, D., and Weise, A., Chern. Ber. 100, 3747 (1967). 28. Masaki, M., Fukui, K., and Ohta, M., J. Org. Chern. 32, 3564 (1967). 29. Neidlein, R., and Heukelbach, E., Arch. Pharrn. 299, 709 (1966). 30. Neidlein, R., and Haussmann, W., Arch. Pharrn. 300,180 (1967). 31. Neidlein, R., and Haussmann, W., Arch. Pharrn. 300, 553 (1967). 32. Neidlein, R., and Heukelbach, E., Arch. Pharrn. 300, 567 (1967). 33. Nikolajewski, H. E., Dlihne, S., and Hirsch, B., Chern. Ber. 100,2616 (1967). 34. Ochiai, M., Kagaku No Ryoiki 19, 900 (1965); Chern. Abstr. 66, 32076 (1967). 35. Ogden, P. H., and Mitsch, R. A., J. Arn. Chern. Soc. 89, 3868 (1967). 36. Ogden, P. H., and Mitsch, R. A., J. Arn. Chern. Soc. 89, 5007 (1967). 37. Ogden, P. H., J. Chern. Soc. (C), 2302 (1967). 38. Ottmann, G., and Hooks, H., Angew. Chern. 79, 1062 (1967). 39. Ottmann, G., Hoberecht, H., and Hooks, H., Angew. Chern. 79,1063 (1967). 40. Ottmann, G., and Hooks, H., J. Heterocycl. Chern. 4, 365 (1967). 41. Pattison, V. A., Colson, J. G., and Carr, R. L. K., J. Org. Chern. 33,1084 (1968). 42. Roesky, H. W., and Biermann, U., Angew. Chern. 79, 904 (1967). 43. Schmelzer, H. G., Degener, E., Holtschmidt, H., and Heitzer, H., Tetrahedron Letters

2801 (1967). . 44. Schmidt, A., Chern. Ber. 100, 3319 (1967). 45. Schmidt, A., Chern. Ber. 100, 3725 (1967). 46. Stojanovic, F. M., and Arnold, Z., Collection Czech. Chern. Cornrnun. 32, 2155 (1967). 47. Thyagarajan, B. S., and Gopalakrishnan, P. V., Tetrahedron 23, 3851 (1967). 48. Tullock, C. W., United States Pat. 3,347,644 (1967).

AUTHOR INDEX

Numbers in parentheses are reference numbers and indicate that an author's work is referred to although his name is not cited in the text. Numbers in italics show the page on which the complete reference is listed.

Abe, J., 62 (223), 110 Acampora, M., 188 (53), 191 Adams, R., 90 (1),105 Adamson, A. B., 177 (28), 178, 184 (27,28),190 Agahigian, H., 207 (34), 209 Akabori, S., 89 (2), 105 Akagi, K., 65, 74, 79 (214), 110 Albers, H., 82 (3), 105 Albright, J. D., 62 (4), 105 Alimov, P., 14, 17, 37, 41 (2),50 Allenstein, E., 13, 50, 66 (6), 79 (5-8), 105,

119 (1, 2), 136, 139, 143, 145 (1), 148 (1), 154,216 (1), 218

Amstutz, E. D., 4 (2, 25), 11;201 (50),210 Anders, B., 13 (95a), 14 (3, 4,5,7, 95a), 17 (4, 5,

93, 95a), 18, 30, 31 (95a), 32 (93, 95a), 33, 34,35,36 (4, 95a), 37 (3, 5, 7, 95a), 38 (95a), 41 (6),43 (5, 95a), 48 (95),50,52

Anker, R. M., 90 (10), 105 Anneser, E., 169 (26), 171 Anschiitz, R., 198 (1), 208 Antia, M. B., 24, 38 (8), 50 Arbasino, M., 168 (1,12),170 Arbuzov, A. E., 85 (11),105 Archer, L., 62, 90 (86), 107 Armand, J., 4 (16),11,159 (2, 54), 164 (53,54),

170,171 Arnold, Z., 62 (12, 16), 64 (12, 23, 25, 27), 81

(22),88,90 (19, 26, 30), 91 (12, 19),92 (12, 13, 15, 17, 18), 94 (12, 13, 14, 18, 29), 95

(18, 28, 154), 96 (20, 21), 100 (27), 105, 106,108,214 (46), 219

221

Ashworth, D. R., 179 (32), 190 Aston, J. G., 71, 76, 80 (127),108 Attaway, J. A., 26, 31 (9),50 Aufderhaar, E., 182, 186, 188 (67, 68), 191 Avogadro, L., 164, 166 (3),170 Aumann, A., 85 (299), 112 Aumiiller, W., 115 (4), 123 (3,4), 126 (4), 136 Aylward, J. B., 178, 181, 183 (95), 193, 217 (19),

218 Bacon, R. G. R., 28, 32, 49 (10), 50, 140, 146,

148 (2),154 Badger, G. M., 90 (31), 106 Baer, K., 82 (91),107 Balszuweit, A., 180, 189, 190 (73), 191 Balucani, D., 90 (236), 110 Banks, R. E., 29, 31 (11),50 Barnish, I. T., 183, 184, 187, 189 (1), 190, 217

(2),218 Barr, D. A., 29, 31, 39 (13), 47 (12), 50 Bartulin, J., 120 (25),136 Bauer, E., 168, 172 Bayer, 0., 15 (88, 99), 22 (99), 32 (100), 40 (88),

42 (99), 49 (99), 52, 132 (35),136, 150 (17), 155

Beck, F., 3 (19), 11 Becker, H., 90 (287), 112 Bedford, M. A., 175, 181 (97), 192 Beer, L., 208 (2) Bell~fontaine, A., 88 (35), 106 Behringer, H., 84 (33, 34), 106 Benn, M. H., 158,165 (4), 170 Benz, E., 62 (4),105

222

Bernhard, c., 91 (130), 108 Bernheimer, 0., 203, 208 Bernthsen, A., 83 (36), 106 Betz, W., 64 (280), 111 Beyer, K. H., 86 (37), 106 Bianchetti, G., 175, 182 (51), 186 (4, 52), 190,

191 Biermann, U., 211 (42),212 (3), 218, 219 Bigelow, L. A., 26, 31 (9),50 Biltz, H., 66 (38), 67, 106 Bloom, E., 181 (71), 191 Bly, R. S., 13, 16 (14), 23, 50 Bock, G., 213 (4),218 Bode, K. D., 84 (293),112 Bodendorf, K., 66, 95 (39), 106, 215 (24), 219 Bodnarchuk, M. D., 68 (186,251), 109,111 Bohme, H., 65 (40), 106 Bohrmann, L., 164 (55),171 Bornowski, H., 40 (38), 51 Boshagen, H., 59 (41), 106,218 (5) Bosshard, H. H., 7 (1), 11, 62 (42), 75 (43), 78

(42,43),79 (43),82 (42), 88 (89), 103, 106 Bost, R. W., 90 (307),112 Bottler, R., 65, 77, 79 (219), 110 Bowack, D. A., 175, 178, 182, 184 (5),190 Brace, N. 0., 66 (44), 106 Brachwitz, H., 160, 161, 164 (5),170 Braid, M., 23, 31, 46 (45), 51 Brannock, K. c., 98 (45), 99 (45), 106 Braun, v. J., 58, 59 (51, 55, 56, 58, 65, 60, 61, 67),

60 (56, 59), 61 (57, 59, 63, 65, 68, 69), 62 (50,64),74 (56), 75 (56, 58,61,64,68), 76 (64), 77 (66), 85, 87 (60, 70), 97, 98 (48, 49, 50, 52-54, 61), 99 (45), 101 (56), 104, 106, 203,208

Bravo, P., 188 (53), 191 Bredereck, H., 62 (71, 73, 75), 85 (71), 88 (72),

89 (75), 90 (74), 93 (76), 106 Bredereck, K., 62 (73), 106, 118 (6), 120, 126 (5),

129, 131 (6), 133 (5, 6), 133 (6), 135 (6, 7), 136

Brendle, T., 135 (7),136 Brintzinger, H., 32 (15), 50 Brower, K. R., 4 (2), 11 Brown, M., 65 (78), 87 (78), 107 Brownell, W., 90 (79), 107 Buijle, R., 99 (80), 107 Biilow, c., 175 (6-17), 178 (6-8, 10, 13, 17),

179 (7), 182 (6-8, 16), 183 (11, 12, 14), 184 (6-10,14,17),185(15),186(7),190

Author Index

Burgess, J. M., 177, 178, 179, 181, 184 (18,19), 190

Burkhardt, J., 36, 40, 42 (16), 50,212 (6), 218 Burpitt, R. D., 98 (45), 99 (45), 106 Busch, M., 102 (81), 107 Buss, H., 158, 166 (66),172 Buu-Hoi, N. P., 90 (82-85, 236), 107, 110 Bykhovskaya, E. G., 29, 31 (68),51 Cadiot, P., 92 (233), 110 Calligaris, M., 218 (7) Campaigne, E., 62, 90 (86), 107 Campbell, R. H., 62 (9), 105 Caputo, J. A., 90 (141), 108 Caramella, P., 217 (8), 218 Carr, R. L. K., 215 (41), 219 Casnati, G., 159 (6),170 Castro, A. J., 90 (112),107 Cerniani, A., 4 (3),11,201 (5),208 Chapman, A. W., 96, 107 Chattaway, F. D., 175 (22, 24), 177 (20-23, 28),

178, 179 (24), 180 (24,26,29), 181 (20-22), 182 (24), 184 (20-22, 27, 28, 30, 31, 33), 187 (22, 23),190

Christi, M., 8 (6), 11, 169 (27), 171 Chrz, J., 175, 182 (43), 191 Ciamician, G. L., 198 (6), 208 Ciba, 90 (89), 107 Ciusa, R., 181 (34), 190 Clark, R. H., 66 (273), III Clovis, J. S., 182, 186, 188 (35),190 Coffman, D. D., 28, 39, 41 (146), 46 (34), 50,

54,69 (277), 100 (114, 115), 107,111, 122, 124, 129 (58), 137

Coleman, G. H., 71, 76 (90), 107 Colson, J. G., 215 (41), 219 Cook, A. H., 90 (10),105,195, 197 (7), 208 Cordes, G., 103 (191), 109 Corell, M., 90 (287),112 Corey, E. J., 62 (144), 108 Cramer, F., 82 (91), 104, 107 Crisafulli, M., 168 (62),172 Claisen, L., 160 (7), 170 Cronin, D. A., 30, 38 (136a), 53, 183 (93, 94),

185 (94), 192 Crouch, W. W., 203 (8, 9), 209 Cumm, G., 168 (63, 64), 172 Curtin, D. y, 82, 83 (93), 107 Diihne, S., 215 (33), 219 D'Alcontres, G. S., 8 (12), 11, 168 (8, 48), 170,

171

Author Index

Daldy, F. G., 175, 179, 180, 182, 190 Dallacker, F., 89, 90 (94),107 Dalla Croce, P., 186 (4), 190 D'Amico, J. J., 62 (9), JU5 Damrauer, R., 28 (138), 53 Danyluk, S. S., 66 (163-165), 108 Dateo, G. P., Jr., 158, 165, 169 (11),170 Daughhetee, P. R., Jr., 47 (59), 51 Dean, 1. M., 90 (129),108,158,159 (19),160

(17),163 (19),171 Decombe, J., 67 (96), 107 Degener, E., 14, 15, 17,33 (17, 54a), 50, 51,57,

60 (152), 66, 67 (305), 72 (97-99, 244), 77 (98), 86 (97, 99, 244), 107, 108, 1I0, 112, 211 (43),219

Dennstedt, M., 34 (18), 50 Derkach, G. I., 14 (19,55,56,64), 17 (19, 64),

18 (56), 21 (64), 36 (55, 56), 37, 39, 40, 41, 43 (19, 64, 56), 50, 51, 58 (183-185), 65 (100,183-185),72(100),77 (100,183-185), 81 (101),85 (102),102 (103),107,109,118 (8),124 (8,11), 125 (8,11,12),129 (8), 131, 132 (9,12),134 (13),135 (10, 11), 136,140, 143,144,146 (10), 155, 216 (9), 218

Desai, P., 194 (92), 107 Dettmer, R., 70 (226), 110 Deyrup, J. A., 195 (10,11),197 (11),209 Dickore, K., 14,37 (7), 42, 50 Diebold, J. L., 102 (255),110 Dieckmann, W., 175, 176, 182 (36), 190 Diekmann, J. 43 (2Ia), 56 Dimroth, 0., 88, 107 Dimroth, P., 57,98 (106), 107 Dobbie, R. c., 30, 50 Dollfus, W., 161, 162 (45), 171 Dornow, A., 166, 167 (9),170 Douglass, I. 8., 17 (21),50 Drechsel, E., 113, 119, 127, 136 Dresdner, R. D., 26 (156, 158), 29 (23, 159),

31 (23, 156--158), 32 (158), 46 (22, 156, 157),47 (157,158),50,54

Dubenko, R. G., 175 (37-39), 182 (37, 39), 184 (38), 191

Dunaevska, T. S., 45 (126), 53 E.1. DuPont de Nemours & Co., 118, 124 (20),

136 Durell, W. S., 122, 124 (72,73),137 Duquette, L. G., 217 (10, 11),218 Dyatkin,8. L., 158, 161, 162, 166 (10),170 Dyson, G. M., 17 (24, 26), 18,34 (24), 39,40

(24,25),43 (24), 48 (25),50, 143, 154 Eckell, A., 182, 186,188 (35), 190

223

Effenberger, F., 62, 89 (75), 106, 135 (7), 136 Eilingsfeld, R., 62 (107,109, 110),63 (109), 78

(107, 109), 81 (107-109), 82 (107), 83, 84 (109),85 (107, 109,296),86 (37, 107, 109), 87 (109), 88 (107, 109, 110), 89 (107), 92 (297),101(110),106,107,132 (69),137,113, 115,116, 117,118,127, 128, 129, 130, 132, 133 (15,16),136,141,146,149,150,151, 152,153 (4, 5), 154

Eistert, B., 91 (III), 107 Elix, J. A., 90 (31), 106 Emeleus, R. J., 30, 50, 122 (17), 136 Engler, R., 175, 178, 183, 184(13, 14), 190 Ermili, A., 90 (112), 107 Eschelbach, F. E., 89,90 (94),107 Etling, R., 24 (43), 51, 65 (136), 108 Ettlinger, M. D., 158, 165, 169 (11),170 Eue, L., 15 (27, 88), 40 (27), 43 (92), 50, 52,

124 (36), 132 (35), 136, 150, 151 (16, 17), 155

Evans, R., 180, 181, 183 (71, 72), 191 Evdokimov, U., 175, 182 (40),191 Farbenfabriken Bayer, A. G., 14 (32), 15 (29),

17 (32), 21 (31, 32), 22 (31), 32, 37 (32), 41 (30), 43 (28, 30), 48 (33), 50, 92, 93 (113), 107, 123 (19), 124 (18), 136

Farinholt, L. R., 180 (26), 190 Favorskii, O. Y., 90 (229), 110 Favrel, G., 175, 182 (41~3), 191 Fawcett, F. S., 46, 50,100 (114,115),107 Federmann, M., 41 (6),50 Fedder, J. E., 62 (264), 111 Feher, F., 140, 146, 148 (6), 154 Feinauer, R., 36, 40, 42 (16), 50 Fetzer, U., 3 (19), 11, 62, 64, 74, 75, 76, 80,

86 (280, 281), III Fields, E. K., 195 (7, 12), 197 (7), 208, 209 Fieser, L. F., 90 (116--119),107 Filatov, A. S., 29, 31, 46 (97), 52, 122 (45),

137 Finkbeiner, R., 62 (120), 108 Finzi, P. Y., 168 (12),170 Fischer, K., 166, 167 (9), 170 Fischer, 0.,108 (121) Fischer, P., 121, 122, 126,129 (21), 136 Fischer, R., 81, 82 (122),108 Fleischmann, M., 102 (81), 107 Foa, M., 201 (13),209

224

Folin, 0.,140 (7),154 Foster, M. 0., 167 (13), 170 Franke, W., 92, 95 (310),112 French, J. C., 72, 75, 98, 99, (270, 271), 111 Freeman, R. c., 65 (261),111 Friedel, M. c., 108 Frommeld, H. D., 159 (21), 160 (17, 22), 170

(18),171 Frosin, V. N., 29, 31 (68),51 Fuchs, R., 216 (1), 218 Fujimoto, K., 62 (223), 110 Fujisawa, T., 14 (35, 104-106),33 (35), 40 (35,

104-106),50, 141, 149, 151, 154 (21, 22), 155

Fukui, K., 213 (28), 219 Fusco, R., 8 (11), 11, 165 (14), 168 (46, 47),170,

In 175, 182 (50,51), 184, 185 (46),186 (44-49,52,75),191

Garritsen, J. W., 6 (10), II, 207, 208 (28, 29), 209

Gates, J. W., Jr., 201, 202 (27), 209 Gaudiano, G., 188 (53),191 Gauss, W., 43 (36), 51 Gavin, D. F., 134 (22),136 Gavin, G., 119, 121, 130 (71),137 Gehlen, H., 45 (103), 52 Genel, F., 218 (12) Gerasimov, S. I., 27, 31, 33 (143),53 Gerland, H., 70 (197),109 Gevorkyan, A. A., 158, 161, 162, 166 (10),170 Gibson, M. S., 177 (19, 54), 178 (18, 54), 179

(19),181 (18, 19,56),184 (18,19),187,189 (1),190,191,217 (2),218

Ginsburg, V. A., 29, 31, 46 (97), 52, 122 (45), 137

Glemser, 0.,212 (3), 218 Gloede, J., 140 (8),155 Gluesenkamp, E. W., 207 (14), 209 Godefroy, E. F., 61 (124),108 Gold, H., 104, 108 Goldman, L., 62 (4), 105 Golovaneva, A. F., 29, 31,46 (97), 52,122 (45),

137 Gompper, R., 14, 16,37,42 (37), 62, 85 (71), 88

(72),106 Gopalakrishnan, P. V., 214 (47), 219 Grashey, R., 181, 182, 186, 188 (65, 66a, 67),

191 Grdinic, M., 62 (137), 79 (126), 85 (137), 100,

108

Author Index

Green, M., 27 (37a), 51 Greenberg, B., 71, 76, 80 (127), 108 Greenwald, R. B., 195, 197 (10, 11),209 Grill, W., 66, 80 (187),109 Grisley, D. W., 207 (14), 209 Gross, H., 40 (38), 51, 140 (8),155 Groth, R. H., 26, 31 (9),50 Griinanger, P., 168 (1), 170 (1, 15), 189 (57),

191 Grundmann, C., 68 (128), 90 (129), 108, 158

(19,20),159 (19, 21),160 (16, 17, 19,22), 163 (19),170 (18),171,198,199,204,205 (46),207 (22, 34),209,210,212 (13), 218

Gubnitskaya, E. S., 85 (102), 102 (103),107 Guette, J. P., 159 (2), 170 Guillemard, H., 15,51 Gulbins, E., 36,40,42 (16), 50 Gulbins, K., 51, 40 (40) Gumpert, F., 18, 19,51 GUnther, H., 158, 162 (76, 77), 172 Gysin, H., 43 (42),51,125 (23), /36 Haack, A., 88, 90 (285), 111 Haan, de J., 208 (15), 209 Hack, H., 15,42 (27),50 Hafner, K., 91 (130-134), 108 Hagedorn, I., 24 (43), 51, 62 (135), 65 (13t ,108 Hahn, V., 62 (137), 79 (126), 85 (137), 100, 108 Hall, D., 214 (14), 218 Hall, H. K., Jr., 62 (138, 139), 108 Halleux, A., 99 (80), 107 Hallmann, F., 62 (140), 80, 108 Hals, L. J., 30, 31 (125a), 53 Hamada, T., 49 (119),53 Hamann, K., 36 (16),40 (16, 40), 42 (16), 50,

51,212 (6), 218 Hamilton, C. S., 178, 182, 185 (96), 192 Hansen, H. K., 90 (141, 188), 108, 109 Hantzsch, A., 40 (44), 51, 66 (142), 108, 119,

127 (24),136, 140, 141, 145, 150 (8a), 155 Hardy, E. M., 117, 128 (42), 132 (43),137 Harrington, T., 17 (24, 26), 18, 34, 39, 40, 43,

48 (24, 25), 50, 143, 154 Harris, F. W., 175, 181 (,,,1),192 Hartke, K., 65 (4O~ 106, 120 (25, 27), 121 (27),

132 (26, 28),136,216 (15), 218 Hartmann, H., 180, 182 (76),191 Hartung, W. H., 164 (29), 171 Hartwell, J. L., 90 (117), 107 Hasek, W. R., 90 (225), 110 Hasserodt, U.,215,218

Author Index

Haszeldine, R. N., 29, 31, 39, 47 (11-13), 50 Haupter, F., 107 Hauptschein, M., 23,31,46 (45, 46), 51 Hauser, L., 84 (33), 106 Haussmann, W., 14 (111, 114, 115), 16 (110,

111), 17 (114), 20, 21, 33 (112), 36 (114), 37 (111,115),39 (111,115),41 (114, 115), 43 (110, 114-116),44 (115), 47 (112, 114), 49 (115), 53, 126, 129, 131 (47), 137, 144, 147, 148, 150, 151, 153 (26-28), 155, 211 (31),212 (30, 31),219

Havlik, A. J., 142, 147 (9),155 Hazebroucq, G., 214 (17), 218 Hegarty, A. F., 177, 191, 217 (18, 19),218 Heine, H. W., 195, 197 (16), 209 Heininger, S. A., 207 (14), 209 Heitzer, H., 211 (43),219 Held, P., 81 (143),108 Helmers, 0.,18,51 Hershberg, E. B., 90 (116), 107 Hertler, W. R., 62 (144), 108 Hesse, H., 71 (213), 110 Hetherington, H. c., 119, 127 (49),137 Hettler, H., 81 (145),108 Heukelbach, E., 14, 16, 37, 39, 41, 43, 44, 45,

49 (113, 115, 117),53, 144, 147, 148, 150, 151 (28), 155,211 (32),215 (29),219

Heymons, A., 59 (55, 60), 60 (59), 61 (57, 59), 97 (60), 106

Hickmott, P. W., 90 (146),108 Hiebsch, A., 91 (276), 111 Hilgetag, G., 103 (147, 315),108,112 Hinga, F. M., 92 (224), 110 Hinkel, L. E., 66 (148), 68, 108 Hirsch, B., 215 (33), 219 Hisada, K., 130 (33), 136 Ho, T., 27 (72), 52 Hoan, N., 90 (82-85), 107 Hoberecht, H., 217 (39), 219 Hochtler, A., 169 (73),172 Hoechster Farbwerke, 89 (152),108 Hoesch, K., 96, 108 Hoff, van der, J. P. H., 208 (15), 209 Hofmann, A. W., 201 (17), 209 Hoffmann, F. W., 23, 31, 39 (105), 54 Hoffmann, M., 57, 63 (289), 112 Holland, N. M., 183, 187 (92), 192 Holsten, J. R., 82 (150), 108 Holtschmidt, H., 14 (49, 54a), 15 (17, 27,144),

17 (17), 20 (49),21 (49-52, 54), 22 (49-54),

225

23 (49, 144),25 (49), 26 (49, 53), 29 (49), 32 (49-52, 1(0), 33 (17, 54a), 34 (49), 35 (49, 52), 42 (27), 50, 51, 52, 53, 57, 60 (152), 72 (97-99, 244), 73 (151,152),74,75 (152), 77 (98), 86 (97, 99, 244), 107, 108, 110, 123, 124, 126 (29), 136,205 (18), 209, 211 (43), 219

Holy, A., 64 (23, 25), 94 (29), 95 (154). 105, 108 Holzweissig, E., 86 (201), 97,109 Homeyer, B., 15 (48),51 Hooks, H., 17, 18 (122), 19 (123), 34 (121), 35

(121, 124),43 (124), 53, 140, 143 (29, 30), 144, 146, 147, 148, 149 (30, 31), 153 (31, 32,34),154,155 (32, 33, 34a), 217 (38-40), 219

Hornung, K. H., 92, 95 (311),112 Houben, H., 162 (24), 171 Howard, E. G., Jr., 66, 67 (155),108 Howe, E. E., 90 (250), 111 Hudson, R. F., 3, 11 Huehsam, G., 93 (300), 112 Huffman, K. R., 123, 127 (30), 136 Huisgen, R., 8, 11, 100 (156, 157), 108, 169

(25-27), 171, 174 (59, 69), 175 (64), 176 (59), 180 (59, 70), 181 (66a, 69), 182 (35. 59-70), 186 (35, 60-70), 187 (61-63), 188 (35,60-70),189 (64, 69),190,191

Humble, H., 180, 183 (72), 191 Humphries, J. E., 180, 181, 183 (71, 72), 191 Hurst, G. L., 122 (17),136 Huss, R., 175, 178, 183, 184 (10, 11), 190 Husted, D. R., 122 (34),136,216 (22), 219 Hyugaji, T., 14,40 (104, 106),52, 149 (21),155 Ichimura, K., 71, 86 (158), 108, 195, 196, 197

(19),209 Illuminati, G., 4, 11,218 (7, 12, 20, 21), 218,

219 Irving, H., 180 (29), 190 Irwin, R. S., 28, 32, 49 (10), 50, 140, 146, 148

(2),154 Isacescu, D., 90 (220), 110, 160 (36), 171 Ishikawa, S., 84, 108 Issleib, K., 180, 189, 190 (73), 191 Ito, Y., 49 (119), 53, 92 (160,162),95 (160, 222),

102 (162, 221), 108, 110 Ivanova, Zh. M., 14, 18, 36, 43 (55, 56), 51,

140, 143, 144, 146 (10),155 Janssen, P. A., 61 (124), 108 Janz, G. J., 66 (163-165),108 Jarovenko, N. N., 17 (56a), 51

226

Jentzsch, W., 24 (57,58),51,65 (166, 169, 170), 85 (167), 86 (168), 108, 109

Johnson, B. A., 92 (224),110 Johnson, F., 66, 67, 69 (171,172),109,217 (10,

11),218 Johnson, H. W., Jr., 47, 51 Johnson, T. B., 17 (21), 50 Jones, J. E., 90 (118), 107 Jostes, F., 59, 60, 74, 75 (55, 56), 90 (173), 101

(55, 56), 106, 109 Jiirgens, B., 160, 162, 164 (57), 171 Jungermann, E., 27 (60),51 Junker, P., 75, 98, 99 (237), 110 Justoni, R., 186 (44,74,75),191 lutz, c., 88 (174), 91 (175,176, 178),93 (1'77),

109 Kadaba, P. K., 195 (20), 209 Kaji, A., 32, 35, 39,40 (61), 51 Kalenda, N. W., 15,32 (141), 53 Kalischer, G., 89, 90 (179), 109 Kamensky, H., 57 (292), 112 Kato, M., 14 (73,78,81),43 (73), 48 (78, 81), 52,

125 (32), 136 Katsuragawa, S., 92 (160, 162),95 (160, 222),

102 (162,221),108,110 Kauer, l. c., 45 (62), 51 Kauffman, H., 162 (24), 171 Kaufmann, H. P., 28 (63), 51 Keller, K., 89, 90 (179), 109 Kern, J., 90 (95), 107 King, E., 175, 182 (16),190 King, W. J., 90 (180, 181), 109 Kinney, C. R., 163 (28), 171 Kirfnskaya, L.I., 17 (56a), 32 (154), 51, 54 Kirsanov, A. Y., 14, 17,21,37,40,41,43 (64),

51, 58, 65 (183-185), 68 (186, 251), 77 (183-185), 81 (101), 85 (102), 102 (103), 107, 109, 118, 124 (8), 125 (8, 12), 129 (8), 131,132 (9,12),136

Kirsanova, N. A., 14, 18, 36,43 (55, 56), 51, 140, 143, 144, 146 (10), 155

Klages, F., 66, 80 (187),109 Klamann, D., 195 (21), 209 Klauke, E., 15 (65), 30, 45 (66, 67), 46 (65), 51,

124 (36), 136 Kleineberg, G., 122 (31), 136 Klemm, K., 62, 85, 88 (71, 72),106 Klutchko, S., 90 (188), 109 Knaak, J., 212 (3), 218 Knuesli, E., 43 (42), 51,125 (23), 136

Author Index

Knunyants, I. L., 29, 31 (68),51,158, 161, 162, 166 (10), 170

Knupfer, H., 175 (64), 181 (66a), 182 (64, 65, 66a), 186 (64, 65, 66a), 188 (64, 65, 66a), 189 (64), 191

Kober, E., 134 (22), 136, 198, 199, 204, 205 (46),207 (22, 34),209,210

Koch, H. J., 174, 176, 180, 182 (59),191 Kochendorfer, G., 62 (239), 89, 110 Kodama, Y., 14 (69-83), 23 (76), 27 (69, 72),

40 (70, 82), 41 (74, 77, 83), 42 (77), 43 (73, 79,80),48 (71, 75, 78, 81), 51, 52,125 (32), 136, 142 (14), 145 (13), 147 (14), 154 (12), 155

Koddebusch, H., 32 (15), 50 Koehler, c., 62 (253), III Konig, c., 91 (133), 108 Kohl, K., 84 (33), 106 Koike, E., 90 (189), 109 Kornilov, M., 95 (28), 105 Kotjscheff, T., 62 (190),109 Koshar, R. J., 122 (34), 136,216 (22), 219 Kosloski, c. L., 113, 117, 119, 127, 128, 132

(41-43),137 Kranz, J., 69, 112 Kresze, G., 213, 219 Kreutzkamp, N., 103 (191),109 Krieble, Y. K., 66 (192),109 Krollpfeiffer, F., 180, 182, (76),191 Kriiger, P., 172 Krueger, R. A., 71, 82 (204), 109 Kiihle, E., 13 (86, 95a), 14 (3, 4, 5, 7, 85, 86, 95a),

15 (27,48,65,88,94,99),17 (3-5,93, 95a), 18 (95a), 19 (85), 22 (99), 23, 24 (86), 30 (66, 95a), 31 (95a), 32 (85, 93, 95a, 100), 33 (85, 95a), 34 (84-86), 35 (84, 86, 95a), 36 (4, 95a), 37 (3, 5, 7, 95a), 38 (84, 95a), 39 (87), 40 (86-88), 41 (6, 86), 42 (27, 86, 89,90, 91, 94, 99, 101), 43 (5, 36, 86, 92, 95a), 44 (86), 45 (66), 46 (65), 47 (86), 48 (95),49 (86, 99, 101),50,51,52,62 (193), 85 (194), 109, 124 (36, 37), 130 (38), 132 (35), 136, 137, 142, 143 (18), 145 (15), 146, 147 (18),150 (16,17),151 (16), 155

Kuhn, M., 113, 119, 127, 129 (39), 137 Kukhar, Y. P., 68 (252), 111 Kukota, S. N., 217 (25), 219 Kunz, R., 14, 16,37,42 (37), 51,181,182,186,

188 (66a, 67), 191 Kurtz, P., 104 (69), 106

Author Index

Kvitko,1. Y., 90 (22a), 110 Laasch, P., 66 (208), 110 Lamonica, G., 168 (8, 63, 64), 170, 172 Lander, G. C., 100 (195),109 Lang, W., 92, 93 (312),112 Langbein, G., 90 (287), 112 Langella, M. R., 170 (15),189 (57), 191 Lanzilotti, A. E., 62 (4), 105 Lapworth, A., 175, 178, 182, 184 (5), 190 Latscha, H. P., 118 (40), 137 Laws, H. E., 100 (195), 109 Lecher, H. Z., 113, 117, 119, 127, 128, 132 (41-

43),137 Lengfeld, F., 113, 119,137, 140, 141, 145 (20),

155 Leo, H., 83 (196), 109 Lepesa, A. M., 81 (101), 107 Lerkova, L. N., 14, 17,37,41 (2),50 Lesinska, J., 195 (25),209 Leuchs, H., 70 (197,198),109 Levin, N., 164 (29),171 Levy, P. R., 71, 76 (199),109,202 (203), 209 Lewis, G. E., 90 (31), 106 Lewis, W. L., 13, 16, 23 (14),50 Ley, H., 86, 87,97 (200, 201),109,158,164,166,

167 (30), 171 Lichtel, E., 24 (43), 51,65 (136),108 Liepe, J., 28 (63), 51 Lilyquist, M. R., 82 (150), 108 Linda, P., 218 (20), 219 Liptuga, N.I., 14, 17,21,37,39,40,41,43 (19,

64),50,51, 134 (13), 136 Lochte, H. L., 203 (8, 9), 209 Lonza, Ltd., 39, 40 (96), 52 Lopatinskaya, N. A., 183, 184, 185 (84), 192 Lorenz, H., 88 (35), 91 (202), 106, 109 Lossen, W., 159 (32),171 Liitzbeyer, J., 215 (24), 219 Lozinskii, M. D., 175, 176, 182 (77, 80), 183

(81,84), 184 (78, 84, 85), 185 (77-87), 191, 192,217 (25), 219

Ludsteck, D., 82 (203), 109 Lukasiewicz, A., 195 (24, 25), 209 Lye, R. J., 178, 179,184 (30, 31),190 Mack, W., 169 (25, 26), 171 Madronero, R., 66, 69 (172), 109 Mai, L., 40 (44), 51, 140, 141, 145, 150 (8a), 155 Makarov, S. P., 29, 31, 46 (97), 52, 122 (45),

137 Malinovski, M. S., 17 (98), 52

227

Malz, H., 15 (48, 99),17 (3), 22 (99),32 (100), 42 (99, 101),49 (99, 101),50,51,52

Manasse, 0., 160 (7), 170 Manno, G., 218 (7) Manuelli, 201 (26),209 Marino, G., 4 (7), 11,218 (12,20,21),219 Markgraf, J. H., 182, 186, 187, 188 (61),191 Martin, D., 103 (205), 109, 216, 217 (27), 219 Martin, G., 10,11,80 (206), 109 Martin, M., 10, 11, 80 (206), 109 Martynova, L. c., 29, 31, 46 (97), 52, 122 (45),

137 Masaki, M., 213 (28),219 Mathis, F., 164 (34), 171 Mathis-Noel, R., 164 (34),171 Mayer, R., 66, 95 (39), 106 Mazalov, S. A., 27, 31, 33 (143), 53, 74 (207),

110 McDonald, R. N., 71, 82 (204), 109 McFarland, J. W., 182, 186, 188 (60), 191 McKee, R. H., 119 (56), 137 Mecke, R., 113, 119, 127, 129 (39),137 Meerwein, H., 66 (208), 110 Mega, P., 181 (34), 190 Meiklejohn, R. A., 122 (34),136 Meltzer, R. 1.,90 (141,188),108,109 Mersch, R., 66 (208), 110 Metzger, H., 208 (2) Meyer, W., 170(52), 171 Meyr, R., 64 (278, 279), 111 Michael, A., 66 (209), 110 Michaels, R. J., Jr., 90 (258,301,302),111,112 Migachev, G. I., 104 (267), 111 Miller, L. L., 82, 83 (93), 107 Mini, V., 160 (17),171 Mitin, Y. V., 103 (210), 110 Mitsch, R. A., 31 (102),52, 212, 219 Mitsunobo, 0., 14 (105), 52,141,151,154 (22),

155 Miyazaki, K., 32, 35, 39, 40 (61), 51 Moebius, L., 141, 146, 149, 150, 151, 152, 153

(4,5),154 Moeckel, K., 45 (103), 152 Morrish, W. N., 181, 183,186 (91),192 Mory, R., 7 (1), 11,62,78,82 (42),106,82 (211),

110 Motornyi, S. P., 17 (56a), 32 (154), 51, 54 Muller, A., 65 (40), 106, 108 Muller, c., 62, 98 (50), 106 Muller, E., 104. 11 1

228

Miiller, W., 91 (176, 178), 93 (177), 109 Mukaiyama, T., 14 (35, 104-106), 33 (35), 40

(35, 104-106), 50, 52, 141, 149, 151, 154 (21,22), 155

Mulder, E., 119, 127 (46), 137 Mumm, 0., 71 (213),96, 110 Munch, 59, 60, 74, 75 (56), 106 Murakami, M., 65, 74, 79 (214), 110 Murphy, D. B., 13, 16,34,44 (107), 53 Musante, C., 162, 166 (33), 165 (14), 170, 171,

184,185,186 (45, 46),191 Musliner, W. J., 201, 202 (27), 209 Mutterties, E. L., 28, 39,41 (146),54,69 (277),

111, 122, 124, 129 (58), 137 Naik, A. R., 160 (61), 172 Namanworth, E., 10 (9),11,80 (215),110 Narbut, A. V., 124 (11), 125 (11, 12), 131, 132

(9, 12), 135 (10, 11), 136,216 (9), 218 Nasutavicus, W. A., 66, 67 (171), 109 Navech, J., 164 (34),171 Neher, P. W., 175, 178, 179, 182, 184 (6--9),

185 (88),186 (6--9),190,191 Nef, J. U., 13, 15, 32, 34, 39, 40, 43 (108, 109),

53, 70 (216--218), 110, 140, 142 (23-25), 155,160,166 (35), 171

Neidlein, R., 14, 16, 17,20,21, 33, 36, 37, 39, 41,43,44,45,47,49 (110-118), 53, 65, 77, 79 (219), 110, 126, 129, 131 (47), 137, 144, 147,148,150,151, 153 (26--28), 155

Neimysheva, A. A., 30, 31, 32, 45,46 (127-129), 53

Nenitzescu, C. D., 90 (220), 110, 160 (36), 171 Nerdel, F., 195 (21), 209 Neubauer, G., 82 (203), 109, 115, 117, 118,

127-130, 132, 133 (16), 136 Neupert, H. J., 91 (276), 111 Newhall, W. F., 119, 128, 129 (48),131 Nikolajewski, H. E., 215 (33), 219 Nohira, H., 14 (106), 52 Nord, F. F., 90 (180, 181), 109 Obayashi, K., 90 (189), 109 Ochiai, M., 214 (34), 219 Oda, R., 49 (119), 53, 92 (160, 162), 95 (160,

222), 102 (161, 162, 221,222), 108, 109 Offermann, K., 64 (280), 111 Ogden, P. H., 31 (102),52,212,219 Ohta, M., 71, 86 (158), 108, 195-197 (19), 209,

213 (28), 219 Oka, R., 90 (189), 109 Okano, M., 49 (119), 53, 92 (160, 162),95 (160,

Author Index

222), 102 (161, 162, 221, 222), 108, 110 Okawa, K., 62 (223), 110 Oster, R., 82 (3), 105 Ostermayer, H., 61, 75 (68), 106 Ottenheym, J. H., 6 (10), 11, 207, 208 (28, 29),

209 Ottmann, G., 17-19, 32-35, 43 (120-124),53,

140, 143 (29, 30), 144 (31), 146--149 (30, 31), 153 (31, 32, 34), 154 (32, 33, 34a), 155, 217 (38--40), 219

Palazzo, G., 170 (37, 38), 171 Palou, E., 120, 126, 129 (27), 136 Pandit, M. I., 24, 38 (8), 50 Parlovskaya, I. V., 29, 31, 46 (97), 52 Passerini, R., 4 (3), 11, 201 (5), 208 Paquette, L. A., 92 (224), 110 Parham, W. E., 90 (225), 110 Parkers, G. C., 184 (33),190 Parlovskaya, I. V., 122 (45), 137 Pasedach, H., 81 (122),82 (122, 203), 108, 109 Pattison, V. A., 215 (41),219 Paul, H, 70 (226), 103 (147, 315), 108, 110, 112 Paul, R., 162, 163 (38, 39), 171 Pawellek, D., 14, 17,28, 36 (125), 53 Pearlson, W. A., 30, 31 (l25a), 53 Pechmann, H. V., 57, 97, 110, 174, 180, 183

(89, 90), 192 Peiker, A. L., 66 (192), 109 Pelkis, P. S., 45 (126),53,175 (37-39, 77),176

(77), 182 (37-39, 77), 183 (81, 84), 184 (38, 78,84,85), 185 (77-87),191,192,217 (25), 219

Perkins, G. A., 13, 16,23 (14),50 Perold, G. W., 158 (40),171 Petersen, S., 66, 67 (305), 112 Peterson, S. W., 80 (228), 110 Petrov, K. A., 30, 31 (128), 32 (127), 45, 46

(128, 129),53 Pfannstiel, K., 32 (15), 50 Pfister, R., 14,27,43 (133), 53 Piloty, 0.,158,162,167 (41), 171 Pink, L. A., 119, 127 (49), 137 Pinkemelle, W., 62, 75, 76 (64), 106 Pizzotti, R., 186 (48),191 Platz, L., 175, 176, 182 (36), 190 Ploss, G., 91 (133), 108 Pocar, D., 186 (4,52),190, 191 Pollock, J. M., 28, 32, 49 (10), 50,140, 146, 148

(2),154 Pommer, H., 85 (299), 112

Author Index

Ponzio, G., 162 (42, 43),171 Poos, G.I., 119, 128, 129 (48),137 Porai-Koshits,8. A., 90 (229, 230), 110 Prajsnar, 8., 62, 73 (231, 232), 208 (30),209 Prandtl, W., 29 (130), 53, 161, 162 (44, 45), 171 Pullin, A. D. E., 28, 32, 49 (10), 50, 140, 146,

148 (21), 154 Pyle, R. E., 71, 76 (90), 107 Quang, Y. V., 92 (233), 110 Quilico, A., 8 (12), 11, 168, 170 (46-48), 171 Quis, P., 66, 79 (6, 8), 105, 139, 143, 145 (1),

154 Raab, R., 100 (157), 108 Rlitz, R., 81 (234, 235), 110, 198, 199,204,205

(46),207 (22, 34),209,210 Rajagopalan, P., 168 (49), 171 Rapoport, L., 207 (36), 209 Recchi, 20 (26), 209 Reiche, F. V. K., 158 (40), 171 Reilly, J., 181, 183, 186 (91),192 Reinhard, W., 104 (92), 107 Reisch, J., 90 (246), 110 Rempfer, H., 62, 85 (61), 106 Rheinboldt, H., 158, 160, 163 (50, 51), 171 Ricca, A., 159 (6), 170 Ricci, A., 4 (13, 14), 11, 90 (236), 110, 201 (13,

31-33), 209 Richter, R., 93 (76), 106, 118, 120, 126, 129,

l3l-133, 135 (5, 6),136,212 (13), 218 Ried, W., 75, 98, 99 (237), 110 Riethman, J., 14,27,39 (131), 53 Rittner, S., 104 (92),107 Robinson, M. A., 134 (22), 136 Roder, T. M., 90 (225), 110 Roesky, H. W., 211 (42),219 Rogers, M. A. T., 90, 91, (240), 110 Roh, N., 62, 89, 90 (238, 239), 110 Romani, R., 175, 186 (49),191 Rosen, I., 33, 34,47 (132), 53 Rosenau, J. D., 119, 128, 129 (48),137 Rossi, S., 175, 182, 184 (50),191 Rudavskii, V. P., 58 (104),107 Rudolph, W., 59 (61), 61 (63, 65), 75 (61), 77

(66),87 (70), 96, 98 (61), 104 (63), 106 Rumpf, J., 43 (42),51,125 (23),136 Rusche, J., 40 (38), 51 Ryskiewicz, E. E., 62 (253), III Salim ann, A., 14 (133), 27 (133), 43 (133),53 Samuels, P., 4 (2), 11 Sandri, J. M., 195,209

Sanova, S. N., 185 (79, 83, 87), 191, 192 Santos, A. A., 93 (77), 106 Sasse, K., 42 (89), 52

229

Sauer, J., 182, 186, 187, 188 (60, 62),191 Sayigh, A. A. R., 6 (20), 7 (22-24), 8 (15, 21, 22),

10 (21),11,14, 19 (148), 20 (147,148, 151), 24 (134),33 (148),53,54,63,64 (282, 283), 65 (241), 82 (283a), 83 (283b, 284), 110, 111,115-118 (59--66),119 (51, 59-66),121, 122, 126, 127-l3l, 133 (59-66), 134 (51, 61,62,65,66),137, 140 (36),155, 199 (49), 200 (47-49), 210

Sauermilch, W., 119 (50), 137 Schaefer, F. C, 123, 127 (30), 136 Schand, E. W., 66, 110 Scheurer, G., 85 (299), 112 Scheyer, H., 89,90 (179), 109 Schicke, H. G., 84 (243), 110 Schliitzer, A., 70 (198), 109 Schmelzer, H. G., 14,15,17,33 (17, 54a), 44

(135),50,51,53,57,60 (152), 72 (97, 99, 244), 73, 74, 75 (152), 77 (98), 86 (97, 99, 244), 107, 108, 110, 211 (43),219

Schmid, M., 7 (1), 11,62,78 (42), 82 (42, 211), 106,110

Schmidt, A., 13, 50, 79 (5, 7), 105, 214 (44), 216 (45), 219

Schmidt, E., 16,32,33 (136), 53 Schmidt, R., 182, 186, 188 (65), 191 Schmitt, J., 92, 93 (312), 112 Schmitz-Dumont, 0., 160 (50), 171 Schnabel, W. J., 134 (22), 136 Schoenleben, W., 86 (260), III Schroeder, H., 82 (3), 105, 198, 199, 204, 205

(46),207 (22, 34),209,210 Schroeter, G., 87 (245), 110, 198 (1), 208 Schulte, K. E., 90 (246), 110 Schurig, H., 93 (300), 112 Scott, F. L., 30, 38 (136a), 53, 177, 178, 181,

183, 185-187 (58, 91-95), 191, 192, 217 (18,19),218

Seeberger, L., 174, 180 (90),192 Seefelder, M., 62, 63 (107-110), 65 (170), 78, 81

(107-110),82 (107, 203, 247), 83, 84 (107-110),85 (107, 109, 167),86 (107, 109, 168, 248),87-89, 101 (107-110), 107, 109, 111, 113,115-118,127-130,132,133 (15,16), 136,137

Seide, S., 68 (128), 108 Seidel, F., 175, 185 (15),190

230

Seidel, M., 175, 181, 182, 186--188 (60--66a),

191 Sekiba, T., 14 (72), 23 (76), 27 (72), 40 (70, 82),

41 (77, 83),42 (77), 43 (73), 48 (71, 73, 75, 81), 51, 52, 125 (32), 136, 142, 145, 147, 154 (12-14),155

Sell, E., 13, 15,39,40,43 (137),53 Sennewald, K., 29 (130), 53,161,162 (44),171 Senoh, J., 89 (2), 105 Seus, E. J., 91 (249), 111 Seyferth, D., 28 (138), 53 Shabica, A. c., 90 (250), 111 Sharp, D. B., 178, 182, 185 (96), 192 Shchekotikhin, A. K., 29, 31, 46 (97), 52, 122

(45), 137 Sheppard, W. A., 18,45 (62),51,53 Shevchenko, V. I., 68,186 (251, 252), 109, 111 Shinohara, S., 14, 43 (79, 80), 52, 130 (33), 136 Shipton, G. 0., 39, 40, 41, 43 (140),53,125 (53),

137, 141 (35), 155 Shishkin, V. E., 85 (11), 105 Shpanskii, V. A., 29, 31, 46 (97),52, 122 (45),

137 Shutkova, E. A., 90, 92, 94 (230), 110 Silber, P., 198 (6), 208 Silverman, R., 59, 75 (58), 106 Silverstein, R. M., 62 (253), 111 Simchen, G., 62 (75), 69 (254), 89 (75), 90 (74),

106,111,205,206 (35), 209 Simmons, T. c., 23,31,39 (155), 54 Skiba, W., 158, 165, 167 (68), 172 Sleiter, G., 4 (7), 11, 218 (20),219 Smissman, E. E., 102 (255), 111 Smit, J. A. R., 119, 127 (46), 137 Smith Ill, A. B., 195, 197 (16), 209 Smith, E. W., 163 (28), 171 Smith, F. W., 15, 27 (60), 51 Smith, G. F., 62 (256),111 Smith, L. R., 61, 65, 74, 75 (265), 83 (262-265),

111 Smith, P. A. S., 15, 32 (141), 53 Smith, T. D., 62, 80 (257), 111 Smith, W. R., 40 (142), 53, 140, 141, 145, 150

(35a), 155 Smolin, E. M., 207 (36), 209 Sobecki, W., 59 (51) Sokolov, S. V., 27, 31, 33 (143), 53, 74 (207),

110 Sommers, A. H., 90 (258), 111 Sonn, A., 104, 111, 170 (52), 171

Author Index

Sorm, F., 88, 91, 92 (94),105 Souchay, P., 4, 11,159,164 (53, 54),171 Spaenig, H., 86 (260), 111 Spengler, W., 175, 178, 184 (17),190 Speziale, A. J., 61, 62, 65, 74, 75, 83 (261-265),

111 Spille, J., 66 (208), 110 Stachel, R. D., 122, 127 (54), 137, 200 (37),

209 Stallings, J. P., 33, 34, 47 (132), 53 Stamicarbon, N. V., 71 (266), 111, 207 (38), 209 Stangl, R., 100 (156), 108 Staskun, B., 71, 111 Steinbock, R., 158, 162, 167 (41),171 Steindorff, A., 113, 118 (55), 137 Steinkopf, W., 160, 162 (56), 164 (55-58), 171 Stepanov, B. I., 104 (267), 111 Stephen, R., 71 (199, 269), 76 (199), 109, 111,

202 (23, 39), 209 Stephen, R. J., 96, 111 Stephen, T., 202 (39), 209 Stevens, C. L., 72, 75, 98, 99 (270, 271),111 Stevens, T. E., 72 (272), 111 Stewart, R., 66 (273), 111 Steyn, A. P., 158 (40), 171 Stieglitz, J., 113, 119 (56),137,140,141,145

(20), 155 Stille, J. K., 175, 181 (97),192 Stock lin, E., 82 (211), 110 Stoess, U., 90 (246), 110 Stoffel, P. J., 117 (57), 137 Stojanovic, F. M., 214 (46), 219 Stolle, R., 180 (98), 192 Streeck, R., 90 (287), 112 Sturm, H. J., 100, 108, 182, 186, 187, 188 (61,

63),191 Suh, J. T., 119, 128, 129 (48), 137 Sustman, R., 180, 182, 186, 188 (70), 191 Sutcliffe, R., 29, 31 (11),50 Sutherland, J. K., 165 (59), 172 Suzuki, K., 199, 209 Sweeting, O. J., 81 (234, 235), 110 Tafel, J., 80 (274),111, 198,209 Takada, H., 90 (189),109 Takahashi, K., 65, 74, 79 (214),110 Talaty, C. N., 168 (49), 171 Tamura, Y., 14, 33,40 (35), 50 Tarnow, R., 15,23 (144), 53 Taura, S., 90 (189),109 Tavolo, G., 164, 166 (3),170

Author Index

Tchelitcheff, S., 162, 163 (39), 171 Tetenbaum, M. T., 208 (42),209 Thiele, J., 30, 38 (145),53,54 Thulke, K., 16, 32, 33 (136), 53 Thurman, J. c., 62 (275), 111 Thyagarajan, B. S., 214 (47), 219 Tiemann, F., 172 (60) Tilley, J. N., 63 (282), 111, 115, 117-119, 134,

137 (51, 62), 137 Tipping, A. E., 27 (37a), 51 Tishler, M., 90 (250), 111 Tlumac, F. N., 29, 31 (23),50 Todesco, P. E., 4 (13, 14, 17, 18), 11, 201 (13,

31-33,43-45),209 Tonges, H., 62 (135),108 Treharne, G. J., 66, 68 (148), 108 Treibs, W., 91 (276), 111 Truce, W. E., 160 (61),172 Tscherniak, M., 15 (145a), 54 Tsoukalas, S. N., 26,31,32,46,47 (156, 158),

54, 122, 124 (73), 137 Tucker, B., 7, 8, 10 (21-23), 11, 82, 83 (283-

284),111, 115 (119, 122, 126-131), 134 (65), 137, 140 (36),155

Tullock, C. W., 28, 29, 41 (146), 46 (34), 50, 54,69 (277), 100 (114, 115),111, 122, 124, 129 (58), 137,211 (48),219

Twine, C. E., 62 (9), 105 Tyulenev, S. S., 85 (II), 105 Uehara, K., 130 (33),136 Ugi, I., 3, 11,62,64,74,75,76,80,86 (278-281),

111 Ulm, K., 195 (21), 209 Ulrich, H., 6, 7, 8,10 (20-24),11,14,18,19,20

(147-151), 24 (134), 33 (148), 53, 54, 63, 64 (282, 283), 65 (241), 82, 83 (282-284), 110, Ill, 115, 116, 118 (59-67), 119 (51, 59-<i7), 121, 122, 126-131, 133 (59-67), 134 (51, 59-67), 137, 140 (36), 155, 198, 199, 200, 204, 205 (46-49), 207 (22, 34), 209,210

Ulrich, M., 158 (31),171 Umani-Ronchi, A., 188 (53),191 Ummat, P. K., 214 (14), 218 Unterstenhoefer, G., 15,23 (144), 53 Valentini, F., 4 (16), 11, 159 (2, 54), 164 (54),

170,171 van der Eycken, C. A. M., 61 (124), 108 Vanghelovici, M., 181 (99), 192 Vecchio, G. L., 168 (8, 62-<i4), 170, 172

Verry, c., 67 (96), 107 Viehe, H. G., 99 (80),107 Vigevani, A., 186 (4), 190

231

Vilsmeier, A., 88, 90 (285, 286), 108, Ill, 112 Vivarelli, P., 4 (13, 14, 17, 18), 11,201 (13,31-

33,43-45),209 Vlasov, G. P., 103 (210), 110 Vogt, A., 119, 127 (24), 136 Vollmann, H., 90 (287),112 Vopel, K. H., 91 (131, 133), 108 Wache, H., 195 (21), 209 Wade, K., 214 (14), 218 Wagenhofer, H., 100 (156),108 Wakefield, B. J., 158, 162, 163 (75), 172 Wald, M. M., 142,147 (9), 155 Walker, A. J., 175, 177, 181, 184, 187 (20-23),

190 Wallach, 0., 57, 63 (289), 83 (288), 85, 97,112 Wallbillich, G., 175 (64), 182, 186, 188 (35, 60,

64,68,70),189 (64),190,191 Walter, W., 84 (293),112 Wardill, J. E., 3 (4), 11 Warren, W. H., 24 (152), 54, 65 (295), 112 Wassmuth, 0., 80 (274),111,198,209 Watanabe, T., 62 (223),110 Way, J. W., 4 (2), 11 Weber, D., 84 (34), 106 Weber, H., 140, 146, 148 (6), 154 Weberndorfer, V., 174, 181 (69), 182, 186, 188,

189 (35, 69),190,191 Webster, S. T., 62 (9), 105 Wegler, R., 14, 19,32,33,34 (85), 52, 124, 130

(37, 38), 137 Wegmiiller, H., 14,27,39 (131), 53 Wei!3ach, K., 85, 106 Weidinger, H., 62, 63, 78,81 (107-110),82 (107,

295), 83, 84 (107-110), 85 (107, 109, 296), 86-89 (107-110),92 (297), 101 (110), 110, 112, 113, 115-118, 127-130 (15, 16), 132 (15, 16,69), 133 (16), 136, 137

Weingarten, H., 135, 137 Weise, A., 70 (226), 103 (205), 109, 110, 216

(26,27),219 Weise, W., 85 (299), 112 Weiser, D., 141 (37), 155 Weissauer, H., 141 (37), 155 Weisse, G., 68 (128),108 Weissenfels, M., 93,112 Wellcome Found. Ltd., 40 (153), 54 Wellenreuther, G., 82 (295),112

232

Werner, A., 158, 163-167 (65-69), 172 Westfall, P. A., 90 (112), 107 Weston, A. W., 90 (79,258, 301, 302), 107, 111 Weygand, C, 168, 172 White, W. A., 135, 137 Wicks, Z. W., 90 (1),105 Widdowson, D. A., 165 (59), 172 Wieland, H., 169 (71, 73), 172 Wiley, R. H., 158, 162, 163 (75), 172 Will, W., 115 (70),137 Willard, C, 62 (253), 111 Willemart, A., 92 (233), 110 Willey, A. R., 163 (28), 171 Williams, J. M., 80 (228), 110 Willis, C J., 29, 31, 39 (13), 50 Wilson, CD., 90 (303, 304), 112 Wilson, F. E., 24 (152), 54, 65 (294), 112 Wing, J. F., 66 (209), 110 Winthrop, S. 0.,119,121,130 (71),137 Wizinger, R., 88 (35), 91 (292), 106, 109 Wolf, F., 62 (190),109 Wolf, W., 66, 67 (305), 112 Wolff, P., 90 (306),112 Wolter, G., 62 (190),109 Wood, J. H., 90 (307),112 Wooley, C, 163 (28), 171 Womer, H., 185 (88), 192

Wright, CD., 216 (22), 219 Wucherpfennig, W., 213, 219 Wulkow, G., 70 (197),109

Author Index

Yakubovich, A. Y., 29, 31,46 (97), 52,122 (45), 137

Yaroslavsky, S., 101 (308),112 Yarovenko, N. N., 32 (154), 54 Young, J. S., 23, 26 (155-159), 29 (23,159),31,

32,39,46,47 (155-159), 50, 54, 122, 124 (72, 73), 137

Young, T. E., 4 (25),11,201 (50),210 Zaoral, M., 103, 112 Zecher. W., 21. 22, 26, 32, 35 (52, 53), 51 Zemlicka, J., 92 (13-15, 17). 94 (13). 96 (20),

105 Zhuravleva, L. P., 118, 124, 125, 129 (8), 136 Ziegenbein, W., 90, 92, 93, 95 (310-314), 112 Ziegler, E., 122 (31),136 Ziegler, J. B., 90 (250), 111 Zieloff, K., 103 (147,315),108,112 Zierold, G., 13, 15,39,40,43 (137), 53 Zinner, G., 158,162 (76, 77), 172 Zoeppritz, 88, 107 Zollinger, R., 7 (1), 11, 62, 75, 79, 82, 88, 103

(42,43), 106 Zumach, G., 13, 14, 17, 18, 30-38, 43, 48 (95a),

52

SUBJECT INDEX

Headings and subheadings in italics refer to working examples.

Acetophenone phenyl hydrazone, bromina-tion, 179

Acid halides, solvolysis, 3 N-Acylcarbodiimides, synthesis, 215 Acyl carbonimidoyl dichlorides, table, 36 Acyl hydrazidoyl halides, table, 182 N-Acylnitrile imides, synthesis, 187 Aldehydes, from imidoyl chlorides, 104 --, synthesis, 88-96 Aldoximes, chlorination, 158 Aliphatic carbonimidoyl dichlorides, table, 32 Aliphatic formam ides, chlorination, 24 Aliphatic hydroxamoyl halides, table, 162 Aliphatic isocyanates, dichlorination, 72 Alkyl halides, from imidoyl halide, 98 Allophanoyl chlorides, synthesis, 118 Amides, degradation, 97, 98 --, reaction with carbonyl chloride, 62, 63 --, reaction with phosphorus pentahalides,

57-61 Amines, chlorination, 73, 205 Arenesulfonylcarbonimidoyl dichlorides,

table, 37 Arenesulfonylchloroformamidines, table, 126 N-Arenesulfonyl-1-halothioformimidates,

synthesis, 144 Aromatic carbonimidoyl dichlorides, table, 34 Aromatic hydroxamoyl halides, table, 163 Aroylhydroxamoyl chlorides, synthesis, 160,

161 ----, table, 164 N-Arylbenzhydrazidoyl bromides, general pro­

cedure of synthesis, 178 Arylcarboxylic acid hydrazides, reaction with

phosphorus pentachloride, 174

Aryl cyanates, reaction with hydrogen chloride, 216

Arylhydrazones, halogenation, 176-179 Arylsulfonyl isocyanates, chlorination, 21 Arylsulfonyl isothiocyanate dimers, synthe-

sis, 42 Azines, chlorination, 180 Azo compounds, halogenation, 179

Beckmann rearrangement, 71 Benzalaniline, reaction with iminium

chlorides, 92 Benzaldehyde 4-nitrophenylhydrazone,

bromination, 178 Benzaldehyde phenylhydrazone, bromination,

176,177 Benzaldehyde o-tolylhydrazone, chlorination,

177 Benzenesu/fon ylc yclohex ylcarbodiimide, 44 Benzhydroxamoyl chloride, reaction with tri­

phenylphosphorous, 170 Benzimidazoles, from o-phenylenediamine

and arylcarbonimidoyl dichlorides, 44 Benzonitrile, from benzhydroxamoyl chloride,

170 Benzoyl isocyanate, reaction with phosphorus

pentachloride, 20 Benzyl isocyanate, chlorination, 20 v. Braun degradation, 7, 97, 98 2-Bromoacetophenone oxime, reaction with

triphenylphosphorus,213 4-Bromophenylcarbonimidoyl dibromide,

synthesis, 24 1-Bromothioformimidates, table, 145

233

234

Caprolactam, reaction with phosgene, 207 --, reaction with phosphoryl chloride, 208 Carbamates, reaction with acid halides, 9,140 Carbamoyl chlorides, chlorination, 73, 205 Carbodiimide, addition of oxalyl chloride, 200 --, from chloroformamidine hydro-

chlorides, 8, 130 --, reaction with carboxylic acid chlorides,

120-122 --, reaction with iminium chlorides, 92 --, synthesis from trichlorophosphazene,

20 Carbonimidoyl dibromides, table, 38 Carbonimidoyl dichlorides, Friedel-Crafts re­

action, 48 ----, reaction with acid anhydrides, 47 ----, reaction with acid hydrazides,

semicarbazides, thiosemicarbazides, 45 ----, reaction with alcohols, 39, 40 ----, reaction with alkoxide ion, 141 ----, reaction with amide oximes, 212 ----, reaction with epoxides, 49 ----, reaction with ethylene glycol, 40 ----, reaction with hydrogen fluoride,

30,45 ----, reaction with hydrogen sulfide, 41 ----, reaction with mercaptans, 41 ----, reaction with primary amine

hydrochlorides, 43 ----, reaction with thiolate ion, 142 ----, reaction with water, 39 Carbonimidoyl difluorides, dimerization, 30,

122 ----, synthesis, 18,23 ----, table, 31 Carbonimidoyl dihalides, infrared spectra, 38,

39 ----, reaction with amines, 43, 44 ----, use as agricultural chemicals, 15 Carboxylic acid hydrazides, reaction with

phosphorus pentabromide, 175 Chapmann rearrangement, 213, 214 Chattaway-Adamson rearrangement, 178 2-Chloroaziridines, nucleophilic substitution

reactions, 197 3-Chloro-I,2-benzisoxazole, nucleophilic sub­

stitution reactions, 218 2-Chlorobenzoxazole, nucleophilic substitu­

tion reactions, 201 2-Chlorobenzthiazole, nucleophilic substitu-

Subject Index

tion reactions, 201 l-Chlorocarbonyl-2-chloro-4,5,6,7-tetrahydro-

lH-azepine,208 Chlorodimethylformiminium chloride, 63 ----, NMR spectra, 10,80 ----, reaction with acetylenes, 92 ----, reaction with alcohols, 81, 82 ----, reaction with diazoketones, 214 ----, reaction with ethylene oxide, 95 ----, reaction with hydrogen cyanide, 96 ----, reaction with ketones, 92-95 ----, reaction with methylenecyclo-

hexan,91 ----, reaction with propioveratrone, 95 ----, reaction with sodium malonate, 93 2-C hloro-l ,3-dimeth ylimidazolidinium

chloride, 200 Chloroformamidine-N-carbonyl chlorides, syn­

thesis, 6, 116 ----, reaction with arylamines, 133 Chloroformamidine hydrochlorides, elimina­

tion of hydrogen chloride, 8, 114, 119 ----, reaction with phenylhydrazine, 133 ----, reaction with sodium hydrogen

sulfide, 132 ----, reaction with water, 129, 130 ----, table, 127 Chloroformamidines, infrared spectra, 128,

129 --, NMR spectra, 128, 129 --, reaction with amines, 132 --, reaction with phenols, 131 --, reaction with phosgene, 6, 116 ----,reaction with water, 129, 130 --, solvolysis, 4 --, table, 124 Chloroformamidinium chlorides, reaction

with alkoxide ion, 130 ----, reaction with diethyl iminocar­

bonate, 216 I-Chloroformimidates, reaction with alkoxide

ion, 150 --, reaction with oximes, 151 --, table, 145 --, thermolysis, 141 Chloroiminium chlorides, general procedure of

synthesis, 63 Chloromethylcarbonimidoyl dichloride, syn­

thesis, 22 4-Chlorophenylcarbonimidoyl dichloride, 24

Subject Index

----, reaction with triethylphosphite, 49 1-p-Chlorophenylsulfonyl-2-ethyl-3-n-propyl­

pseudourea, 131 P-Chloropropionimidoyl chloride, synthesis,

66 Chlorosulfonyl isocyanate, chlorination, 211 l-Chlorothioformimidates, table, 146 l-Chlorothioformimidinium chlorides, 141 ----, hydrolysis. 149 ----, reaction with acid hydrazides, 152 ----, reaction with amines, 151 ----, reaction with phenols, 150 1-(Chlorothio)formimidoyl chlorides, addi-

tion to isocyanates, 153 ----, addition to olefins,18,149,153 ----, addition to vinyl ethers, 217 ----, 1 : 1 adducts, 18 ----, reaction with aldehydes, 217 ----, reaction with arylalkylketones, 154 ----, reaction with isothiocyanates, 18 ----, synthesis, 18, 143, 144 ----. table. 146 5-C hlorotol ylene-2 ,4-bis( 1,3 -diet hylene-

guanidine), 43 p-Chlorovinylaldehydes, synthesis, 93 Cyanamide, addition of hydrogen halides, 119 Cyanogen chloride, addition to carboxylic

acid chlorides. 28 ----, addition to sulfur dichloride, 28 ----, reaction of SF sCI with, 28 Cyanogen chloride, tetrameric, 14,27 Cyanogen-di-N-oxide, reaction with hydrogen

bromide, 160 Cyanuric chloride, reactivity of chloro groups,

206 Cyclic amidines, from iminium chlorides, 86 Cyclopentadiene, formylation, 91

Dialkylcarbodiimides, general procedure of syn­thesis. 134

Dialkylcyanamides, reaction with carboxylic acid chlorides, 120

Diaminocyclopropanes, from iminium chlorides, 102

Diazaphosphetidinones, synthesis, 118 Diazonium chlorides, reaction with ethyl

diazoacetate, 176 Diazonium halides, reaction with haloketones,

175,176

N,N' -Di-n-butylchloroformamidine hydro­chloride, 119

235

Dichloroacetylcarbonimidoyl dichloride, 17 2,2-Dichloroaziridines, nucleophilic substitu-

tion reactions, 196 --, synthesis, 194, 195 --, thermolysis, 195 tX,tX-Dichlorobenzylcarbonimidoyl dichloride,

synthesis, 17 Dichlorocarbene, addition to aliphatic carbo­

diimides. 28 --, addition to azomethines, 71 tX,tX-Dichlorocarbonimidoyl dichlorides, syn­

thesis, 21, 47 2,2-Dichloroimidazolidine-4,5-diones, table,

127 1,3-Dichloroisoquinoline, 206 Dichloromethylcarbonimidoyl dichloride,

synthesis, 22 N -Dichloromethylformamidinium chlorides,

synthesis, 65 Dichlorophosphorylcarbonimidoyl di­

chloride, synthesis, 21 2,4-Dichloro-l,3,5-triazine-6-carbonimidoyl

dichloride, 27 2,4-Dichloro-6-trichloromethylphenyl­

carbonimidoyl dichloride, pyrolysis, 48 N,N'-Dicyclohexylchloroformamidine

hydrochloride, 118 ----, reaction with 1,3-dicyclohexylurea,

134,135 N,N' -Diethyl-N-acetylchloroformamidine, 121 Difluoromethane-l,l-bis-carbonimidoyl

difluoride. photolysis of, 212 N ,N' -Diisopropylchloroformamidine-N­

carbonyl chloride, 121 N,N-Dimethylaminoacetonitrile, chlorina-

tion,26 . p-Dimethylaminocinnamic aldehyde, synthe­

sis, 94 N -(3-Dimethylaminopropyl)carbonimidoyl

dichloride. 15 N,N-Dimethylformamide dimethylacetal, 81 N,N-Dimethylformamide, reaction with cyan­

uric chloride. 104 --, reaction with phosphonitrile chloride,

104 Dimethylketen-p-anisylimine, 99 N,N-Dimethylthioformamide, 84 tX,w-Dinitriles, cyclization, 66--67, 218

236

1,I-Diphenylethylene, formylation, 91

1-p-Ethoxyphenyl-3-phenyl-2,2-dichloro­aziridine, 195

Ethylcarbonimidoyl dichloride, synthesis, 15 Ethyltrichloroacetimidoyl chloride, 60

Fluorodimethylformiminium fluoride, 64 Fluoroformamidines, synthesis, 122 --, table, 124 Formamidine hydrochlorides, synthesis, 65 Formanilide, chlorination, 23 Fulvenes, formylation, 91

2-Halobenzthiazole, reaction with nucleo­philes,4

Q(-Halocarbonimidoyl dichlorides, reaction with amidines, 44

Haloformimidates, infrared spectra, 148 --, reaction with water, 149 Haloquinolines, nucleophilic substitution re-

actions, 218 1,2,3,4,5,6-Hexachlorocyclohexylcarbon­

imidoyl dichloride, synthesis, 47 Hydrazidoyl chlorides, dehydrochlorination,

186-189 ----, reaction with amines, 184 ----, reaction with ammonia, 184 ----, reaction with potassium cyanide,

186 ----, reaction with sodium cyanate, 185 ----, reaction with water, 183 ----, table, 180 Hydroxamoyl chlorides, elimination of hydro­

gen chloride, 168, 169 ----, general procedure of synthesis from

nitrile oxides, 160 ----, hydrolysis, 4, 164 ----, reaction with alkoxide ion, 165 ----, reaction with amines, 166 ----, reaction with ammonia, 166 ----, reaction with azide ion, 167 ----, reaction with hydrazine, 167 ----, reaction with hydroxylamine, 167 ----, reaction with phenylmagnesium

bromide, 170 ----, reaction with the pyridine-SOJ

complex, 169

Subject Index

----, reaction with thiophenols, 165 Imidoyl chloride N-carbonyl chlorides, re­

action of amidines with, 86 Imidoyl chlorides, addition of hydrogen

halides, 100 ----, from nitriles and hydrogen halides,

66-69 ----, general procedure of synthesis, 62 ----, halogenation, 101 ----, isomerization, 59 ----, reaction with amines, 85, 86 ----, reaction with carboxylic acids, 82,

83 ----, reaction with 4-dimethylamino-

phenyllithium, 102 ----, reaction with hydrazines, 86 ----, reaction with hydrogen sulfide, 83 ----, reaction with hydroxylamines, 86 ----, reaction with magnesium halides,

102 ----, reaction with phosphites, 103 ----, reaction with potassium cyanide,

96 ----, reaction with ureas, 86 ----, reaction with water, 80 ----, reaction with xanthates, 85 ----, self-condensation, 59 ----, solvolysis, 3, 80 ----, table, 74--76 ----, via chlorination of azomethines, 70 Imidoyl halides, elimination reactions, 7 ----, infrared spectra, 10, 78-79 ----, isomerization to enamines, 6, 59 ----, NMR spectra, 10 ----, reaction with alkoxide ion, 80-81 Iminium chlorides, from ynamines, 99 ----, halogenation, 101 ----, in peptide synthesis, 103, 104 ----, reaction with acetals, 92, 94 ----, reaction with alcohols, 81 ----, reaction with alkylene oxides, 92 ----, reaction with diazonium salts, 101 ----, reaction with enamines, 90, 91 ----, reaction with isocyanides, 102 ----, reaction with ketals, 92 ----, reaction with mercaptans, 84, 85 ----, self-condensation, 88 ----, table, 78 ----, use as catalysts, 7, 81-83 Isobutylene, formylation, 91

Subject Index

Isocyanates, reaction with phosphorus penta-chloride, 19

2-Isocyanatobenzoyl chloride, synthesis, 83 Isocyanides, addition of acyl halides, 142 --, addition of ethyl hypochlorite, 70, 142 --, addition of halogen, 15 --, from carbonimidoyl dihalides, 49 --, reaction with carbonyl chloride, 70 --, reaction with carboxylic acid chlorides,

70 --, via a-elimination, 64 Isocyanogen tetrabromide, synthesis, 30 Isothiocyanates, addition of hydrocyanic acid,

72 --, chlorination, 16, 17 Isoxazoles, synthesis from hydroxamoyl

chlorides, 168

Ketenimines, addition of chlorine, 72 --, synthesis, 57, 98

Methanesulfonylcarbonimidoyl dichloride, 16 Methylcarbonimidoyl dichloride, 19 N-Methylisatoic anhydride, chlorination, 29 Methyl isothiocyanate, addition of hydrogen

bromide, 143 N-Methylpyrrolidone, high-temperature

chlorination, 211 N-Monosubstituted ureas, reaction with phos­

phorus pentachloride, 63 Morpholine, chlorination, 73

Nitrile imides, cyclization, 187, 217 ----, 1,3-cycloaddition, 186--189 Nitrile oxides, addition of hydrogen chloride,

159,160 ----, 1,3-cycloaddition, 168, 169 ----, reaction with methanesulfonyl

chloride, 160 Nitriles, addition of SF 5CI to, 69 --, from imidoyl halides, 97, 98 --, phosphorylation, 68 Nitrile ylides, synthesis, 100 Nitrilium salts, synthesis, 66

Olefins, formylation, 91 1,3,4-0xadiazoles, synthesis, 187 Oxalic acid 4-nitrophenylhydrazidoyl bromide,

ethyl ester, 178 Oximes, chlorination, 159

237

Pentachloroethyltrichloroacetimidoyl chloride, 60

Pentachlorophenylcarbonimidoyl dichloride, synthesis, 22, 25

Pentafluoroethylcarbonimidoyl difluoride, synthesis, 30

Perfluorinated fluoroformamidines, synthesis, 216

Perfluorocarbonimidoyl difluorides, dimerization, 46

----, synthesis, 29 Perfluorocarbamoyl fluorides, elimination of

carbonyl fluoride, 23 Perfluorohydroxamoyl fluorides, reaction

with hydrogen chloride, 161 Perfluoro-1-piperideine,205 4-Phenylbenzhydroxamoyl chloride, 158 Phenylbenzimidoyl chloride, reaction with

dimethyl sulfoxide, 103 ----, reaction with resorcinol, 96 ----, reaction with sodium thiophenol-

ate, 85 Phenylcarbonimidoyl dichloride, 16 ----, reaction with acetic acid, 40 ----, reaction with benzaldoxime, 45 ----, reaction with sodium azide, 45 ----, synthesis, 13, 16 I-Phenyl-5-chlorotetrazole, reaction with

phenolate ion, 201 Phenyl isocyanate, reaction with iminium

chlorides, 92 Phenyl isocyanide, addition of bromine, 15 ----, addition of iodine, 15 Phenyl isothiocyanate, chlorination of, 15 1-Phenyl-2-methyl-3-dimethylpseudourea, 151 Phenylnitromethane, reaction with hydrogen

chloride, 160 Phenylthioformamide, reaction with bromine,

24 Phosphorylcarbonimidoyl dichlorides, table,

37 Piperidinone, reaction with phosphorus

pentachloride,61 Pseudothiourea, chlorination, 117 Pseudoureas, from chloroformamidine hydro­

chlorides, 130 --, from 1-chloroformimidate, 150

Stilbenes, formylation, 91 Styrenes, formylation, 91

238

N-Sulfinylaniline, reaction with iminium chlorides, 92

N-Sulfinylsulfonamides, reaction with car­boxylic acid chlorides, 213

Sulfonylcarbodiimides, synthesis, 8, 115 Sulfonyl-l-chlorothioimidates, reaction with

sodium azide, 153 Synthesis of peptides, using iminium chlorides,

103

Tertiary amines, chlorination, 26 Tetrachloroethane 1,2-bis-carbonimidoyl di­

chloride, 26 Tetrafluoropyrimidine, reaction with nucleo­

philes,207 Tetrakis(dimethylamino)methane, synthesis,

135 N,N,N' ,N' -tetramethy lethylenediamine,

chlorination, 26 N,N,N',N' -Tetramethyl-N" -phenylguanidine,

132 Tetrazoles, from imidoyl chlorides and azide

ion, 87 Thiazetidine-2-ones, synthesis, 115, 116 ThiOlunides, halogenation, 56 Thiocarbamates, reaction with acid halides,

140 Thiocarbarnic acid S-esters, general procedure

of synthesis, 149 Thiocyanates, addition of hydrogen halides,

143 --, synthesis, 142 0-Thiocyanatobenzoyl chloride, reaction with

hydrogen chloride, 69 Thioformimidates, infrared spectra, 148 Thioureas, reaction with carbonyl chloride,

114-117 N -p-Toluenesulfon yl-N' -n-butylchloroforrna­

midine, 115

Subject Index

p-Toluenesulfonylcarbonirnidoyl dichloride, re­action with thiophenol, 42

1,3,5-Triazines, from nitriles, 68 Triazinyl isocyanate, from tetrameric cyano­

gen chloride, 48 Triazinyl isothiocyanate, from tetrameric

cyanogen chloride, 42 2,2,6-Trichloro-3,3,4,4,5,5-hexafiuoro-l­

piperideine, 205 Trichloromethylcarbonimidoyl dichloride,

synthesis, 22 Trichloronitrosomethane, thermolysis, 29 2,4,6-Trichlorophenylcarbonimidoyl

dichloride, synthesis, 25 Trichlorophosphazenes, synthesis, 58 2,3,6-Trichloropyridine, synthesis, 203 2,5,5- Trichloro-3,3,4,4-tetrajiuoro-l-p yrroline,

199 2,3,3-T richloro-3,4,5 ,6-tetrahydropyridine,

synthesis, 203 Trifluorocarbonimidoyl difluoride, synthesis,

26 Trifluoro-1,3,5-triazine, reaction with nucleo­

philes,207 Trimethylacethydroxarnoyl chloride, 158 2,4,6-Trimethyoxybenz-2,4,6-trinitrophenyl­

hydrazidoyl chloride, 174 Tris-formylmethane, synthesis, 96

Ureas, reaction with carbonyl chloride, 117 Uretone imine, reaction with carbonyl

chloride, 123

Vilsmeier-Haack aldehyde synthesis, 88-90 Vinyl ethers, formylation, 91

Ynamines, synthesis, 99