New method of synthesis of beta-haloalkyl alkynyl sulfides: Reaction of alkynesulfenamides with olefins in the presence of phosphoryl halidesстатья
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Дата последнего поиска статьи во внешних источниках: 18 июля 2013 г.
Аннотация:Reactions of alkynelsufenamides with olefins (such as cyclohexene, norbornene, I-hexene, I-octene, allylbenzene, and styrene) in the presence of phosphoryl halides (POCl3, POBr3) afforded 70-95% of beta-halo-substituted alkyl alkynyl sulfides. The reactions with cyclohexene and norbornene are characterized by trans stereoselectivity. Alkynylsulfenylation of terminal alkyl- and benzylacetylenes occurs in a regioselective fashion with predominant formation of the corresponding anti-Markownikoff adducts, while the addition to styrene yields halogen-containing sulfides according to the Markownikoff rule.