Tetrahedron

Azo anions in synthesis: Use of trityl-and diphenyl-4-pyridylmethylhydrazones for reductive CC bond formation

…, RM Adlington, JC Bottaro, JN Kolhe, IM Newington…

Index: Baldwin, Jack E.; Adlington, Robert M.; Bottaro, Jeffrey C.; Kolhe, Jayant N.; Newington, Ian M.; Perry, Matthew W. D. Tetrahedron, 1986 , vol. 42, # 15 p. 4235 - 4246

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Citation Number: 17

Abstract

The lithium salts of trityl-and diphenyl-4-pyridylmethyl-hydrazones of both aldehydes and ketones react with electrophiles (alkyl halides, aldehydes, ketones, crotonates) at low temperature to form C-trapped azo compounds; these Intermediates decompose homolytically with loss of nitrogen below room temperature and can be diverted in a synthetically useful way to alkanes, alkenes, alcohols or saturated esters.