PREPARATION AND REACTIONS OF N,N'-DIACYL-N,N'-DIALKOXYHYDRAZINES

The oxidation of N-acyl-O-alkylhydroxylamines (I) with a number of oxidizing agents was found to give a previously unreported class of compounds, N,Nʹ-diacyl-N,Nʹ-dialkoxyhydrazines (II). The reactions of II can be initiated by nucleophylic attack on carbonyl carbon, electrophylic attack on alkoxy oxygen, or freeradical attack on either alkoxy oxygen or carbonyl carbon. A four-center mechanism for decomposition of II to ester and nitrogen appears to be important in the absence of strong nucleophiles, electrophiles, or free radicals. © 1968, American Chemical Society. All rights reserved.