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Supporting Information for
Synthesis of Ene-yne-enes by Nickel-Catalyzed Double SN2’ substitution of 1,6-Dichlorohexa-2,4-diyne
Gongbao Wanga, Erik-Jan Lindeboom, Chris van Heerewaarden
a, and Adriaan, J.
Minnaarda*
a Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The
Netherlands
E-mail: [email protected]
Table of Contents
Table of Contents S1
Copy of 1H NMR, 13C NMR, APT NMR and IR spectra of compound 1-10 S2
X-ray structure determination of dicobalt complex 10 S16
GC-MS spectra of compound 3-9 S18
Electronic Supplementary Material (ESI) for Catalysis Science & Technology.This journal is © The Royal Society of Chemistry 2017
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1H , 13C, APT NMR and IR spectra
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IR spectrum of complex 10
X-ray structure determination of dicobalt complex 10
Figure S1 Molecular structure of compound 10, showing 50% probability ellipsoids.
Hydrogen atoms are omitted for clarity.
A single crystal of compound 10 was mounted on top of a cryoloop and transferred into the
cold nitrogen stream (100 K) of a Bruker-AXS D8 Venture diffractometer. Data collection and
reduction was done using the Bruker software suite APEX3.1 The final unit cell was obtained
from the xyz centroids of 9770 reflections after integration. A multiscan absorption
correction was applied, based on the intensities of symmetry-related reflections measured
at different angular settings (SADABS). The structures were solved by direct methods using
SHELXT2 and refinement of the structure was performed using SHLELXL.3 The hydrogen
atoms were generated by geometrical considerations, constrained to idealised geometries
and allowed to ride on their carrier atoms with an isotropic displacement parameter related
to the equivalent displacement parameter of their carrier atoms. Crystal data and details on
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data collection and refinement are presented in Table 1. The structure was deposited in the
CCDC deposition number: 1519007.
Table 1. Crystallographic data for dicobalt complex 10
1 Bruker. APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. 2016.
2 Sheldrick, G. M. Acta Cryst. 2015, A71, 3-8.
3 Sheldrick, G. M.. Acta Cryst. 2008, A64, 112-122.
chem formula C24 H14 Co2 O6
Mr 516.21
cryst syst Triclinic
color, habit red, block
size (mm) 0.24 x 0.29 x 0.32
space group P -1
a (Å) 8.4376(11)
b (Å) 10.1022(12)
c (Å) 13.0614(15)
, deg 98.593(4)
, deg 92.973(4)
, deg 100.142(4)
V (Å3) 1080.1(2)
Z 2
calc, g.cm-3
1.587
µ(Mo K ), cm-1
1.574
F(000) 520
temp (K) 100(2)
range (deg) 3.245 – 27.925
data collected (h,k,l) -11:11, -13:13, -17:17
no. of rflns collected 44480
no. of indpndt reflns 5140
observed reflns 4915 (Fo 2 (Fo))
R(F) (%) 1.78
wR(F2) (%) 4.78
GooF 1.057
Weighting a,b 0.0228, 0.5470
params refined 289
restraints 0
min, max resid dens -0.294, 0.361
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GC-MS Spectra
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