Cycloaddition of primary phosphines to divinyl sulfide |
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Authors: | N. K. Gusarova S. F. Malysheva V. A. Kuimov N. A. Belogorlova A. V. Vashchenko B. A. Trofimov |
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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: | Primary phosphines reacted with divinyl sulfide under radical initiation conditions (AIBN, 65–70°C, reactant molar ratio 1:1) according to the addition-cyclization pattern to give 4-substituted 1,4-thiaphosphinanes which underwent almost quantitative oxidation with oxygen or elemental sulfur, yielding the corresponding 4-substituted 1,4-thiaphosphinane oxides (sulfides). The reaction of 4-(2-phenylethyl)-1,4-thiaphosphinane with methyl iodide afforded 4-methyl-4-(2-phenylethyl)-1,4-thiaphosphinanium iodide with high chemoselectivity. |
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