Preparation of 2,4-trans-Flavan-4-ols by oxymercuration-demercuration of Flav-3-enes

Abstract

Oxymercuration-demercuration of flav-3-enes has been found to give 2,4- trans-flavan-4-ols as the major products together with traces of the 2,3-trans-3,4-cis-flavan-3,4-diols. Flav-3-enes having electron-releasing substituents in conjugated positions on the A-ring react less readily than those lacking these substituents. N.m.r. data are presented on the compounds obtained.