AN EFFICIENT ROUTE TO TRANS-4,5-DIHYDROTHIOPHENES AND THIAZOLES VIA NITROGEN AND SULFUR YLIDES

Abstract

A number of versatile sulfonium and pyridinium salts reacted stereoselectively with some arylidenecyanothioacetamides under mild heating to give trans-4,5-dihydrothiophenes. The stereochemistry of the products was established on the basis of X-ray analysis. Repeatingthe same reactions at high temperature furnished a mixture of trans-4,5-dihydrothiophenes and thiazoles.

ACKNOWLEDGMENT

The author would like to thank Prof. Toshio Fuchigami, Tokyo Institute of Technology (TIT), for his kind hospitality. Also, thanks to Prof. Munetaka Akita (TIT), for measuringX-ray crystallography.