Reaction of trithiazyl trichloride with active methylene compounds

CW Rees

Index: Duan, Xiao-Guang; Duan, Xiao-Lan; Rees, Charles W. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 19 p. 2831 - 2836

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Citation Number: 13

Abstract

Activated allylic compounds react with trithiazyl trichloride,(NSCl) 3, to give 1, 2, 5- thiadiazoles 1 and isothiazoles 2. An allylic 2-substituent normally prevents formation of an aromatic 1, 2, 5-thiadiazole, and isothiazole formation becomes the major pathway. Simple allylic compounds are not very reactive towards (NSCl) 3 but a terminal electron withdrawing group (CO2Et) enhances the reactivity. With unsymmetrical allylic compounds, isothiazole ...