SULFONATE ESTERS OF α-CHLOROALDOXIMES, ALDOXIMES, AND AMIDOXIMES VIA "SULFENE" ADDITION

Abstract

Reaction of aromatic nitrile oxides with methanesulfonyl and benzylsulfonyl chlorides in the presence of triethylamine yielded sulfonate esters of α-chloroaldoximes [Formula: see text]. Under the same reaction conditions, aldoximes yielded sulfonate esters, which decomposed to nitriles, and amidoximes yielded amidoxime O-sulfonates, which were also prepared by the action of ammonium hydroxide on [Formula: see text]. Chemical as well as nuclear magnetic resonance spectroscopic evidence confirms the formula [Formula: see text] for amidoximes.