Facile Synthesis of 2,5-Diacylthiophenes. II. The Reaction of Diketo Sulfides with 1,2-Diketones
- 1 April 1980
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 53 (4) , 1187-1188
- https://doi.org/10.1246/bcsj.53.1187
Abstract
The base-catalyzed reaction of diketosulfides (RCOCH2)2S (R=phenyl, p-tolyl) with biacetyl or benzil have provided high yields of 2,5-diacyltetrahydrothiophene-3,4-diol derivatives rather than the expected 2,5-diacylthiophenes. The diols have been transformed cleanly into the corresponding 2,5-diacylthiophenes by treatment with thionyl chloride-pyridine. In contrast, the reaction of the diketo sulfide (R=p-tolyl) with phenylglyoxal afforded a 2,5-diacylthiophene directly in good yield.This publication has 3 references indexed in Scilit:
- Facile synthesis of 2,5‐diacylthiophenesJournal of Heterocyclic Chemistry, 1979
- The Mechanism of the Hinsberg Thiophene Ring Synthesis1,2Journal of the American Chemical Society, 1965
- Oxydation de thiophènes en sulfones propriétés du groupe sulfonyle XXXIVRecueil des Travaux Chimiques des Pays-Bas, 1953