An electron resonance study of some substituted phenoxymethyl radicals

Abstract

A large number of substituted phenoxymethyl radicals formed by the reaction of t-butoxyl radicals with substituted anisoles, thioanisole, phenetole, and thiophenetole have been investigated by e.s.r. The methylene hyperfine couplings are only slightly dependent on the nature of substituents in the aromatic ring; in all cases coupling to ring protons and fluorine atoms has been resolved. The methylene couplings of several of the radicals exhibit linewidth alternation at –35°. Evidence is presented for long-range coupling to ring atoms when ortho-substituents force the methylene group out of the plane of the aromatic system.