The synthesis of NH aldimines and derivatives by spontaneous and base-catalysed decomposition of oxaziridines

Abstract

A range of oxaziridines containing N-methylene substituents has been synthesized by peracid oxidation of the corresponding fluorenylidene N-alkylamines. Spontaneous and tertiary amine base-catalysed decomposition of the oxaziridines into unstable NH aldimines and derivatives was observed. Acrylaldehyde, 2-methylacrylaldehyde, and benzaldehyde NH imines have been identified as initial products from decomposition of the corresponding oxaziridines. 2,4,6-Trialkylhexahydro-1,3,5-triazines, N,N′-dialkylidene-1,1 -diaminoalkanes, N,N′-diarylidene-1,1 -diaminoalkanes, and N-iso-butylidene-2-methylpropenylamine were among the isolated products formed via the undetected alkyl aldehyde NH imines resulting from oxaziridine decomposition.