AZO ANIONS IN SYNTHESIS. USE OF TRITYL- AND DIPHENYL-4-PYRIDYLMETHYLHYDRAZONES FOR REDUCTIVE C-C BOND FORMATION.

Article abstract of DOI:10.1016/S0040-4020(01)87648-1

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.