Selective cross-acyloin condensation catalyzed by thiazolium salt. Formation of 1-hydroxy 2-one from formaldehyde and other aldehydes

T Matsumoto, M Ohishi, S Inoue

Index: Matsumoto, Toshihiko; Ohishi, Masafumi; Inoue, Shohei Journal of Organic Chemistry, 1985 , vol. 50, # 5 p. 603 - 606

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Citation Number: 63

Abstract

The condensation of formaldehyde with another aldehyde catalyzed by 3- ethylbenzothiazolium bromide in the presence of triethylamine gives selectively 1-hydroxy 2- ones. This selective cross-acyloin condensation indicates an inverse selectivity in the reactions of the conjugate base of thiazolium salt 17 and of the carbanion bound to thiazolium ring 19 toward aldehyde.