全氟烷基磺酰溴与杂原子取代烯键的反应

The Reaction of Perfluoroalkanesulfonyl Bromide with Hetero-atom Substituted Olefins

全氟烷基磺酰溴与杂原子取代烯烃,如溴乙烯,乙酸乙烯酯,三甲基硅乙烯加成,得相应的加成物,与烯醇硅醚反应,水解后得到α位溴代酮和全氟烷基亚磺酸.全氟磺酰氯与1-三甲基硅氧基-1-叔丁基乙烯在紫外光照下反应,生成α位全氟烷基化的酮.

Perfluoroalkanesulfonyl bromides reacted with vinyl bromide,vinyl acetate andtrimethyl vinyl silane to give the corresponding adducts with the evolution of SO.However,reaction with trimethyl silyl enol ether followed by hydrolysis gave only thecorrespondingα-bromo ketones and perfluoroalkanesulfinic acids.Perfluoroalkanesul-fonyl chloride reacted with trimethylsilyl ether of pinacolone on UV irradiation to givethe correspondingα-perfluoroalkyl derivative of pinacolone.Under mild condition,perfluoroalkanesulfonyl bromide also brominated phenol and anisole to give thecorresponding p-bromo derivatives.Sodiumα,α-dichlorotrifluoroethane sulfinatereacted with bromine in water at 25℃to formα,α-dichlorotrifluoroethanesulfonylbromide which was thermally less stable than but similar in reactivity to perfluoro-alkanesulfonyl bromide.