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■ Ketone-generationg Reaction of 3-Methyl-2-(1’-hydroxydialkylmethyl)benzothiazolium Iodide under Basic Conditions

Hidenori Chikashita,* Masayuki Ishihara, and Kazuyoshi Itoh

*Department of Applied Chemistry, Faculty of Engineering, Kansai University, Suita, Osaka 564-8680, Japan

Abstract

Quaternized benzothiazol-2-yl moiety was found to be a good leaving group in the ketone-generating reaction of 3-methyl-2-(1’-hydroxydialkylmethyl)benzothiazolium iodides. The benzothiazolium salts easily obtained from ketones via methylation of 2-(1’-hydroxydialkylmethyl)benzothiazoles with methyl iodide, produced the corresponding ketones in excellent yields by the treatment with a variety of bases. Aldehydes and carboxylic esters were convertible to ketones by using the present methodology.