Reactions of t-butyl peroxide with phenols

Abstract

The reactions of free radicals, formed by thermal decomposition of t-butyi peroxide, with phenols has been studied Although the major products were 2,2′-dihydroxy-derivatives of biphenyl the isomeric 2-hydoxydiphenyl ethers were also formed. Pummerer's ketone was not formed, and the isolation of 4,4′-dihydroxy-3,3′-dimethylbibenzyl from the reaction with 2,4-dimethylphenol has shown that coupling via benzyl radicals is nrot restrictedto fully hindered phenols or to 4-methoxytoluene.