The stereochemistry of fragmentation products formed in the lead tetraacetate and related oxidations of alcohols. Part. I. β‐fragmentation of cis‐and trans‐4‐t‐Butylcyclohexanemethanol

Abstract

The stereochemistry of β‐fragmentation products formed in the oxidation of cis‐and trans‐4‐t‐butylcyclohexaanemethanol with lead tetraacetate and with lead tetraacetate‐metal chloride combinations, under various reaction conditions, has been investigated, and the results compared with those obtained, under similar conditions, in the oxidative decarboxylation of cis‐and trans‐4‐t‐butylcyclohexanecarboxylic acid with the same reagents. It was found that all four substrates afford, under comparable conditions, identical cis‐trans proportions of the respective fragmentation products, and that, therefore, so far as steric course is concerned, both the initial homolytic and subsequent heterolytic processes involved in the lead tetraacetate fragmentation reaction are independent of the nature and configuration of the starting material.