Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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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

  • Published : 1997.02.20
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Abstract

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.

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References

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