Non??Dipolar Behavior of Mesoionic Heterocycles: Synthesis and Tautomerism of 2??Alkylthioisomünchnones

M Ávalos, R Babiano, P Cintas, J Díaz…

Index: Avalos, Martin; Babiano, Reyes; Cintas, Pedro; Diaz, Jesus; Jimenez, Jose L.; Lopez, Ignacio; Palacios, Juan C. European Journal of Organic Chemistry, 2004 , # 13 p. 2805 - 2811

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Citation Number: 9

Abstract

Abstract This paper describes a general preparation of a series of 1, 3-thiazolium-4-olates, each bearing an alkyl group at C-2, through reactions between N-arylthiocarboxamides and α-haloacyl halides. Unlike the 2-aryl-substituted derivatives, such alkylated mesoionic compounds exist in equilibria with their non-dipolar tautomers, the corresponding 2- alkylidene-1, 3-thiazolidin-4-ones. The unambiguous characterization of such tautomers ...