Synthetic Application of Benzothiazole Ring System as an On-Off Type of Leaving Group. Synthesis of Ketones and Carboxylic Acid Derivatives from 2-(1-Substituted …

H Chikashita, M Ishihara, K Takigawa…

Index: Chikashita; Ishihara; Takigawa; Itoh Bulletin of the Chemical Society of Japan, 1991 , vol. 64, # 11 p. 3256 - 3261

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Citation Number: 7

Abstract

A synthetic and systematic use of benzothiazole ring system as an “on-off” type of leaving group was developed for the preparation of ketones and carboxylic acid derivatives from a variety of 2-(1-substituted 1-hydroxyalkyl)-and 2-(1-hydroxyalkyl) benzothiazoles (off state) via the corresponding benzothiazolium salts (on state) obtained by the quaternization (on switch). A variety of 3-methyl-2-(1-substituted 1-hydroxyalkyl) benzothiazolium iodides (1) ...