Regio- and stereo-selectivity correlation of the Wittig rearrangement

Abstract

The [1,2]- and [1,6]-rearrangements of s-octyl benzhydryl ether gave products in equal amounts whose formation occurred with 20% retention of configuration, and with complete recemization, for the [1,2]- and the [1,6]-products respectively; these results can be rationalized either by the formation of different non-equilibrating singlet radical pair intermediates, or by an important product formation after diffusion of the intermediate radical pairs.