Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Thiocarbonyl Ylide Intermediates Generated by Deprotonation of 2-Phenacylthio- and 2-(p-Bromophenacylthio)-1,3-dithiolylium and 2-(p-Bromophenacylthio)-1,3-dithiolanylium Bromides
Juzo NakayamaToshiro TakemasaMasamatsu Hoshino
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1980 Volume 53 Issue 8 Pages 2281-2284

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Abstract

2-(p-Bromophenacylthio)-1,3-dithiolylium bromide, when treated with triethylamine, gave 2-(p-bromophenacylidene)-1,3-dithiole (17%) and bis[(p-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-(p-bromophenacylthio)-1,3-dithiolanylium bromide yielded 1-(p-bromophenyl)-2-(1,3-dithiolan-2-yl)-2-thioxoethanone (12%) in addition to 2-(p-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.

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