Thiocarbonyl ylide intermediates generated by deprotonation of 2-phenacylthio- and 2-(p-bromophenacylthio)-1,3-dithiolylium and 2-(p-bromophenacylthio)-1,3-dithiolanylium bromides.

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概要

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• 2-(<I>p</I>-Bromophenacylthio)-1,3-dithiolylium bromide, when treated with triethylamine, gave 2-(<I>p</I>-bromophenacylidene)-1,3-dithiole (17%) and bis[(<I>p</I>-bromobenzoyl)(1,3-dithiol-2-ylidene)methyl] disulfide (72%). Treatment of 2-phenacylthio-1,3-dithiolylium bromide with triethylamine also gave similar results. On the other hand, 2-(<I>p</I>-bromophenacylthio)-1,3-dithiolanylium bromide yielded 1-(<I>p</I>-bromophenyl)-2-(1,3-dithiolan-2-yl)-2-thioxoethanone (12%) in addition to 2-(<I>p</I>-bromophenacylidene)-1,3-dithiolane (49%) contrary to the reported results. These results can best be rationalized by 1,3-cyclization of thiocarbonyl ylide intermediates to the valence tautomeric episulfides.

• 公益社団法人 日本化学会の論文

著者

• Nakayama Juzo

  Department Of Chemistry Faculty Of Science Saitama University

• Hoshino Masamatsu

  Department of Chemistry, Faculty of Science and Engineering, Saitama University

• Takemasa Toshiro

  Department of Chemistry, College of Liberal Arts, Saitama University

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