Acyl iodides in organic synthesis. reaction of acetyl iodide with Dialkyl sulfides and disulfides |
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Authors: | N. N. Vlasova O. Yu. Grigor’eva M. G. Voronkov |
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Affiliation: | 1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia
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Abstract: | Reactions of acetyl iodide with dialkyl and dialkenyl sulfides RSR (R = Et, Bu, CH2=CH, CH2=CHCH2) and with disulfides RSSR (R = Pr, C6H13, PhCH2) were studied. Dialkyl sulfides reacted with MeCOI to give the corresponding alkyl ethanethioates and alkyl iodides as a result of cleavage of the S-C bond. The reactions of acetyl iodide with divinyl and diallyl sulfides involved addition across the double bond and subsequent polymerization of 1-alkenylsulfanyl-2(3)-iodoalkyl methyl ketones. Dialkyl disulfides RSSR (R = Pr, C6H13) and dibenzyl disulfide reacted with acetyl iodide via cleavage of the S-S bond to produce the corresponding ethanethioates and organylsulfenyl iodides. The latter underwent disproportionation to form the initial disulfide and molecular iodine. |
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