Functionalization of alkenes by polyfluorinated α,β-unsaturated sulfenyl chlorides: reactions of 2-chloroperfluoro-1-cyclohexene-sulfenyl chloride-1 with activated olefins

Article abstract of DOI:10.1016/S0022-1139(00)80852-0

A variety of β-chlorothioethers have been obtained by the reaction of 2-chloroperfluoro-1-cyclohexenesulfenyl chloride-1 (I) with t-butylethene, styrene, allylbenzene and p-methoxyallylbenzene in CH2Cl2 or CH3NO2.Skeletal rearrangement with 1,2-migration of the p-methoxyphenyl group occurs on reaction of I with p-methoxyallylbenzene along with the formation of addition products (Markovnikov and anti-Markovnikov adducts).A possible additive salt effect (LiClO4/CH3NO2 system) has been examined for the reaction of I with t-butylethene, allylbenzene and p-methoxyallylbenzene; the effect is noted only in the case of t-butylethene, when intramolecular rearrangement with 1,2-migration of the methyl group takes place.