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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 18, Number 2
BKCSDE 18(2)
February 20, 1997 

Stereochemical Course of the Reductive Decyanation of Cyclic α-Phenylnitrile. Dependence on the Added Alcohol and Metal of the Decyanation of 4-t-Butyl-1-phenylcyclohexanecarbonitrile
Choon Sup Ra, Yang Sook Kim
Stereochemical course of the reductive decyanation of two stereoisomeric 4-t-butyl-1-phenylcyclohexanecarbonitriles 3 and 4 using solvated electron has been studied. While sodium-mediated reactions of both 3 and 4 in the presence of alcohols give the same ratio, 1.5 : 1, in favor of the thermodynamically more stable product 5 over the other one 6, the ratios obtained from the potassium-mediated process are found to be very sensitive to the kind of H-donors. When reactions are performed without H-donors, 5 is only obtained from the experiments with both stereoisomers irrespective of the metal species.
151 - 155
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