Selective formation of five-membered heterocyclic products by anodic oxidation of alkyl isothiocyanates (RNCS) in dichloromethane and their thermal isomerization …

JY Becker, S Yatziv

Index: Becker, James Y.; Yatziv, Shimon Journal of Organic Chemistry, 1988 , vol. 53, # 8 p. 1744 - 1748

Full Text: HTML

Citation Number: 2

Abstract

Anodic oxidation of primary and secondary alkyl isothiocyanates (RNCS) in dichloromethane yielded two isomers of five-membered heterocyclic products, 4-alkyl-5- (alkylimino)-l, 2, 4-dithiazolidine-3-one 2 and 2, 4-di-alkyl-5oxo-1, 2, 4thiadiezolidine-3- thione 3. Their relative ratio was found to be dependent on the length or bulkiness of the alkyl group in RNCS. Isomer 2 was favorable for R= Me and Et and exclusive for R= n-Pr, ...