The alkyl peroxymercuration of terminal alkenes; a synthesis of secondary alkyl peroxides and β-functionally substituted peroxides

Abstract

t-Butyl hydroperoxide reacts with 1-alkenes in the presence of mercuric acetate to yield 2-alkyl-2-t-butylperoxyethylmercuric acetates [Bu^tO·O·CHR·CH₂·Hg·OAc]; the carbon–mercury bond of the product may be cleaved with sodium borohydride or halogens to give good yield of 1-alkylethyl t-butyl peroxide and 1-alkyl-2-halogeno-ethyl t-butyl peroxide, respectively.