Rearrangement studies with 14C. XXIX. The deoxidation of 2-phenyl-1-14C-ethanol

Abstract

The product (styrene) derived from the deoxidation of 2-phenyl-1-14C-ethanol showed 22–26% rearrangement of the 14C label from C-1 to C-2. The extent of this rearrangement is quite close to the values reported for the analogous rearrangement in the deamination of 2-phenyl-l-14C-ethylamine, thus giving further support to the suggested similarity between deoxidation and deamination reactions. The 2-phenylethanol recovered from the deoxidation reaction mixture also showed 3–5% rearrangement of the 14C label from C-l to C-2. This constitutes the first observation of the formation of a rearranged alcohol in a deoxidation reaction. Other mechanistic implications of the results are discussed.