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Induced Alkene Reactions with Sulfur Dichloride. System Sulfur Dichloride-Dimethyl Sulfide as a Reagent for Polysulfonation and Conjugate Chlorination of Alkenes

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Abstract

In reaction of unsaturated compounds with sulfur dichloride in the presence of dimethyl sulfide radically new induced directions are realized: the reagent is involved as dimer or trimer (formation of di- and trisulfides). Alongside this process a conjugate chlorination occurred with participation of external nucleophiles, dimethyl sulfide and acetonitrile, furnishing sulfonium chlorides and N-substituted acetamides respectively. The relative importance of these alternative reactions depends on solvent, alkene structure, and order of reagents addition.

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Authors and Affiliations

  1. Nizhegorodskii State Technical University, Nizhni Novgorod, 603024, Russia

    I. V. Bodrikov, A. A. Sazhin, I. Yu. Shebelova & A. Yu. Subbotin

  2. Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, 630090, Russia

    T. V. Rybalova, Yu. V. Gatilov & V. A. Barkhash

Authors
  1. I. V. Bodrikov
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  2. A. A. Sazhin
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  3. I. Yu. Shebelova
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  4. A. Yu. Subbotin
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  5. T. V. Rybalova
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  6. Yu. V. Gatilov
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  7. V. A. Barkhash
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Bodrikov, I.V., Sazhin, A.A., Shebelova, I.Y. et al. Induced Alkene Reactions with Sulfur Dichloride. System Sulfur Dichloride-Dimethyl Sulfide as a Reagent for Polysulfonation and Conjugate Chlorination of Alkenes. Russian Journal of Organic Chemistry 38, 1105–1112 (2002). https://doi.org/10.1023/A:1020933005986

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