The reaction of α??haloketones with N??alkyl benzothiazolium salts

JA Van Allan, JD Mee, CA Maggiulli…

Index: Van Allan,J.A. et al. Journal of Heterocyclic Chemistry, 1975 , vol. 12, p. 1005 - 1007

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Abstract

Abstract Phenacyl chloride (1a) reacts with the 3-methylbenzothiazolium quaternary salt (2) to give 4-methyl-2-benzoyl-4H-1, 4-benzothiazine (4a). A mechanism is discussed. Secondary α-haloketones give benzothiazolines. Merocyanine dyes are formed by the reaction of 2 with carbanions. It is shown that 2 functions as a hydride ion abstractor in the formation of merocyanine dyes.