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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| Authors: | Bodrikov I V Sazhin A A Shebelova I Yu Subbotin A Yu Rybalova T V Gatilov Yu V Barkhash V A |
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| Institution: | (1) Nizhegorodskii State Technical University, Nizhni Novgorod, 603024, Russia;(2) Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, 630090, Russia |
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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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