
TY  - JOUR
A1  - Jackson, WR 
A1  - Lovel, CG 
T1  - The stereochemistry of organometallic compounds. XXII. The stereochemistry of metal-catalysed hydrogen cyanide addition to olefins
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1982
VL  - 35
IS  - 10
SP  - 2053
EP  - 2067
KW  - 
UR  - https://doi.org/10.1071/CH9822053 
N2  - Reactions of (E)-3,3-dimethyl(1,2-D2)but-1-ene with hydrogen cyanide and of (E)-3,3-dimethyl-(1-D)but-1-ene with deuterium cyanide have been shown to proceed in a completely stereospecific cis fashion when a catalyst system based on Pd(diop)2 was used. Reaction between 4-t-butylcyclo-hexene and deuterium cyanide with the catalyst system gave only the equatorial nitriles trans- 4-t-butylcyclohexane-1-carbonitrile and cis-3-t-butylcyclohexane-1-carbonitrile with cis incorporation of deuterium. Use of a catalyst system based on Ni[P(OPh)3]4 and zinc chloride led to significant amounts of isotopic exchange and rearrangement. These results are compared with those from hydroformylation of the olefins, and the mechanism of hydrocyanation is discussed. 
ER  -

