Iodoacetoxylation of 3-t-butylcyclohexene

Abstract

Iodoacetoxylation of 3-t-butylcyclohexene with silver(I) acetate–iodine or thallium(I) acetate–iodine gives an ca. 3 : 1 mixture of t-2-iodo-t-3-t-butylcyclohexan-r-1-yl acetate and t-2-iodo-c-3-t-butylcyclohexan-r-1-yl acetate as the major products. The ratio is similar to that obtained for the major alcohols from reduction of the iodo-acetates with tri-n-butyltin hydride followed by lithium aluminium hydride, but differs from that obtained by Freppel and Richer for the vicinal diols prepared from a Woodward–Prévost reaction with 3-t-butylcyclohexene. The difference is explained by showing that solvolysis of the diaxial iodo-acetate (2) proceeds in a non-stereospecific manner.