European journal of organic chemistry

Reinvestigation of the Mechanism of gem??Diacylation: Chemoselective Conversion of Aldehydes to Various gem??Diacylates and Their Cleavage under Acidic and …

V Kavala, BK Patel

Index: Kavala, Veerababurao; Patel, Bhisma K. European Journal of Organic Chemistry, 2005 , # 2 p. 441 - 451

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Citation Number: 31

Abstract

Abstract The mechanism of gem-diacylate formation has been studied extensively using tetrabutylammonium tribromide (TBATB) as the catalyst. The reaction proceeds by a nucleophilic attack of an anhydride on an aldehydic carbonyl group, nucleophilic attack of the hemiacylate intermediate on a second molecule of the anhydride, followed by an intermolecular attack of a second acetate group to regenerate the anhydride. gem- ...

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