Singlet oxygen. Conformational requirements for the decomposition of sulphur substituted dioxetans

Abstract

Photosensitized oxygenation of 1-ethylthio-cyclohexene gave a C–C bond cleavage product via an intermediate sulphur substituted dioxetan, but when 1-ethylthio-4-t-butylcyclohexene was used both C–C and C–S cleavage products were produced; the relative cleavage of the C–S and C–C bonds was affected by the conformation of the intermediate dioxetans.