FUNCTIONALIZATION OF ALKENES BY POLYFLUORINATED ALPHA,BETA-UNSATURATED SULFENYL CHLORIDES - DUAL REACTIVITY OF PERFLUORO-2-METHYL-2-PENTEN-3-YL SULFENYL CHLORIDE IN REACTIONS WITH ACTIVATED OLEFINS

A dual reactivity of perfluoro-2-methyl-2-penten-3-yl sulphenyl chlori de (1) in reactions with alkenes is described. Whereas 1 interacts wit h 3,3-dimethyl-1-butene and styrene in nitromethane solution in the su lphenyl chloride form, reactions with olefins that have mobile hydroge n atoms in an allylic position (e.g. allyl- and p-methoxyallyl-benzene s) occur through the tautomeric thioketone form - 2-chloroperfluoro-2- methylpentanethione-3 (3) - with the formation of products by ene rear rangement. Chlorotropism in the system 1 reversible arrow 3 in the pre sence of nucleophilic solvents or catalysts is responsible for the dua l reactivity of 1 in the above reactions.