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Homolytic Reaction of N-Halogenosulphoximides with Olefins and Toluene
Akasaka, Takeshi,Furukawa, Naomichi,Oae, Shigeru
, p. 1257 - 1261 (2007/10/02)
Homolytic addition reaction of N-halogenosulphoximides, i.e. diphenyl-N-chlorosulphoximide (1), diphenyl-N-bromosulphoximide (2), and methylphenyl-N-chlorosulphoximide (3), to olefins such as t-butylethylene and cyclohexene under both u.v. irradiation and thermolysis in the presence of a radical initiator was found to afford the corresponding N-alkylated sulphoximides, which are presumed to be formed via the initial addition of the sulphoximidoyl radical.Meanwhile, homolytic bromination of toluene with N-bromosulphoximide (2) proceeded readily by u.v. irradiation, or by thermal reaction in the presence of a radical initiator, to afford benzyl bromide.However, chlorination of toluene was sluggish with N-chlorosulphoximides (1) and (3). α-Bromination was interpreted in terms of a chain process involving bromine molecules like the 'Goldfinger mechanism', but not via that involving the sulphoximidoyl radical.
