Azo anions in synthesis. t-Butylhydrazones as acyl-anion equivalents

Abstract

The lithium salts of aldehyde t-butylhydrazones react with electrophiles (aldehydes, ketones, alkyl halides) to form C-trapped t-butylazo compounds; isomerisation and hydrolysis gave α-hydroxy ketones and ketones in good yields, thereby providing a convenient new acyl-anion equivalent.