Azo anions in synthesis. Use of trityl- and diphenyl-4-pyridylmethyl-hydrazones for reductive C–C bond formation from aldehydes and ketones
作者:Jack E. Baldwin、Jeffrey C. Bottaro、Jayant N. Kolhe、Robert M. Adlington
DOI:10.1039/c39840000022
日期:——
The lithium salts for trityl- and diphenyl-4-pyridylmethyl-hydrazones of both aldehydes and ketones react with electrophiles (alkyl haldies, aldehydes, and ketones) 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, or alkenes, or alcohols.
Michael additions of hydrazones for carbon–carbon bond formation
作者:Jack E. Baldwin、Robert M. Adlington、Jeffrey C. Bottaro、Ashok U. Jain、Jayant N. Kolhe、Matthew W. D. Perry、Ian M. Newington
DOI:10.1039/c39840001095
日期:——
The lithium salts of t-butyl-and trityl-hydrazones react with methyl crotonate to form C-trapped azo-esters and similar products were observed from a thermal ene-reaction of aldehyde t-butylhydrazones with methyl acrylate or acrylonitrile, and aldehyde phenylhydrazones with methyl acrylate; these products can be diverted into synthetically useful γ-keto-esters, γ-keto-nitriles, saturated esters, γ