Neighbouring-group participation by phenolate in the opening of an epoxide ring

Abstract

o-(2,3-Epoxypropyl) phenol has been detected by n.m.r. spectroscopy as an intermediate in the reaction of o-allylphenol with m-chloroperbenzoic acid to yield 2,3-dihydro-2-hydroxymethylbenzofuran. An impure sample of o-(2,3-epoxypropyl)phenol was isolated and the kinetics of its conversion into 2,3-dihydro-2-hydroxymethyl-benzofuran in aqueous solution were studied. The rate shows a sigmoid dependence on pH and is proportional to the concentration of o-(2,3-epoxypropyl)phenolate.