FUNCTIONALIZATION OF ALKENES BY POLYFLUORINATED ALPHA,BETA-UNSATURATED SULFENYL CHLORIDES - REACTIONS OF 2-CHLOROPERFLUORO-1-CYCLOHEXENESULFENYL CHLORIDE-1 WITH ACTIVATED OLEFINS

A variety of beta-chlorothioethers have been obtained by the reaction of 2-chloroperfluoro-1-cyclohexenesulfenyl chloride-1 (I) with t-butyl ethene, styrene, allylbenzene and p-methoxyallylbenzene in CH2Cl2 or C H3NO2. Skeletal rearrangement with 1,2-migration of the p-methoxypheny l group occurs on reaction of I with p-methoxyallylbenzene along with the formation of addition products (Markovnikov and anti-Markovnikov a dducts). A possible additive salt effect (LiClO4/CH3NO2 system) has be en examined for the reaction of I with t-butylethene, allylbenzene and p-methoxyallylbenzene; the effect is noted only in the case of t-buty lethene, when intramolecular rearrangement with 1,2-migration of the m ethyl group takes place.