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Reactions of Dichlorocarbene and Arenesulfenyl Chlorides with 3,4-Epoxy-1-butene and Vinylethylene Carbonate

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Abstract

Reaction of 3,4-epoxy-1-butene with dichlorocarbene is accompanied by deoxygenation and yields a mixture of 1,1-dichloro-2-vinylcyclopropane, 2,2,2',2'-tetrachlorobicyclopropyl, and 2,2-dichlorocyclopropyloxirane. Arenesulfenyl chlorides react with 3,4-epoxy-1-butene to afford both Markownikoff and anti-Markownikoff addition products, whereas vinylethylene carbonate gives rise exclusively to the anti-Markownikoff adducts.

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Authors and Affiliations

  1. Kazan State University, ul. Kremlevskaya 18, Kazan, 420008, Tatarstan, Russia

    T. G. Mannafov, E. A. Berdnikov & Ya. D. Samuilov

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  1. T. G. Mannafov
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  2. E. A. Berdnikov
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  3. Ya. D. Samuilov
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Mannafov, T.G., Berdnikov, E.A. & Samuilov, Y.D. Reactions of Dichlorocarbene and Arenesulfenyl Chlorides with 3,4-Epoxy-1-butene and Vinylethylene Carbonate. Russian Journal of Organic Chemistry 37, 339–344 (2001). https://doi.org/10.1023/A:1012368021459

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