- New method of synthesis of β-haloalkyl alkynyl sulfides: Reaction of alkynesulfenamides with olefins in the presence of phosphoryl halides
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Reactions of alkynelsufenamides with olefins (such as cyclohexene, norbornene, 1-hexene, 1-octene, allylbenzene, and styrene) in the presence of phosphoryl halides (POCl3, POBr3) afforded 70-95% of β-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.
- Beloglazkina,Belova,Dubinina,Garkusha,Buryak,Zyk
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