
%0 Journal Article
%A Jackson, WR 
%A Lovel, CG 
%T The stereochemistry of organometallic compounds. XXII. The stereochemistry of metal-catalysed hydrogen cyanide addition to olefins
%J Australian Journal of Chemistry
%D 1982/10/01
%V 35
%N 10
%P 2053-2067
%K 
%R https://doi.org/10.1071/CH9822053
%U https://www.publish.csiro.au/paper/CH9822053 
%X 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. 
