Synthesis of. beta.-Dicarbonyl Compounds via the Conjugate Addition of Benzaldoximate Anion to. alpha.,. beta.-Acetylenic Carbonyl Compounds

…, A Perez-Medrano, JM Muchowski

Index: Gomez, Virginia; Perez-Medrano, Arturo; Muchowski, Joseph M. Journal of Organic Chemistry, 1994 , vol. 59, # 5 p. 1219 - 1221

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Citation Number: 14

Abstract

We recently required a method for the conversion of a, O-acetylenic carbonyl compounds into the corresponding 0-dicarbonyl compounds. The transformation of a, & acetylenic esters into 8-keto esters (acids) has previously been accomplished by hydration with alcoholic hydroxide112 or, much more efficiently, by acidic hydrolysis of the acetylene-secondary amine The considerable nucleophilicity of oxime anions7p8 coupled with the facile ...