Tetrahedron

Azo anions in systhesis. pt 1. t-butylhydrazones as acyl-anion equivalents

JE Baldwin, RM Adlington, JC Bottaro, JN Kolhe…

Index: Baldwin, Jack E.; Adlington, Robert M.; Bottaro, Jeffrey C.; Kolhe, Jayant N.; Perry, Matthew W. D.; Jain, Ashok U. Tetrahedron, 1986 , vol. 42, # 15 p. 4223 - 4234

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Citation Number: 36

Abstract

The lithium salts of aldehyde t-butylhydrazones react with electrophiles (aldehydes, ketones, alkyl halides, crotonates) to form C-trapped t-butylazo-compounds; tautomerisation and hydrolysis gave α-hydroxy ketones, ketones, and γ-keto esters in good yield, thereby providing a convenient new acyl-anion equivalent. Reaction of these lithium salts with aldehydes and ketones, followed by elimination provided a new route to azo alkenes.

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