New Method of Synthesis of β-Haloalkyl Alkynyl Sulfides: Reaction of Alkynesulfenamides with Olefins in the Presence of Phosphoryl Halides |
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| Authors: | E K Beloglazkina M A Belova N S Dubinina I A Garkusha A K Buryak N V Zyk |
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| Institution: | (1) Faculty of Chemistry, Lomonosov Moscow State University, Vorob’evy gory 1, Moscow, 119992, Russia;(2) Institute of Physical Chemistry, Russian Academy of Sciences, Leninskii prospect, Moscow, 119991, Russia |
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| Abstract: | 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.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 7, 2005, pp. 977–982.Original Russian Text Copyright © 2005 by Beloglazkina, Belova, Dubinina, Garkusha, Buryak, Zyk. |
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