Generation and some reactions of phenylsulphonylcarbene

Abstract

Phenylsulphonylcarbene has been generated in benzene, in cyclohexene, and in cyclohexane by thermolysis and photolysis of diazo(phenylsulphonyl)methane. Phenylsulphonyl radicals are also formed from the photolyses in benzene and cyclohexane. In benzene, benzyl phenyl sulphone (3) is formed in minor amounts, by substitution and not by ring contraction of 7-phenylsulphonylcyclohepta-1,3,5-triene. In cyclohexene, cyclopropane adducts are formed in an exo : endo ratio of 2.2 : 1.