The Journal of Organic Chemistry

N-(. alpha.-Ethoxyallyl) benzotriazole: A Novel Propenoyl Anion Synthon Route to Vinyl Ketones

AR Katritzky, G Zhang, J Jiang

Index: Katritzky, Alan R.; Zhang, Guifen; Jiang, Jinlong Journal of Organic Chemistry, 1995 , vol. 60, # 23 p. 7589 - 7596

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Citation Number: 33

Abstract

Lithiation with butyllithium of N-(a-ethoxyally1) benzotriazole (2)(readily prepared in quantitative yield on a large scale from benzotriazole and acrolein diethyl acetal (9)) followed by reaction of lithio derivative 14 with halides, a,/?-unsaturated esters, a,/?- unsaturated ketones, and aldehydes gave exclusively a-alkylation adducts. These adducts are hydrolyzed under extremely mild conditions, enabling convenient syntheses of vinyl ...