Asymmetric nonbridging nitrogen 19. Reaction of the o-ethers of activated oximes with diazoalkanes

1. The reaction of the O-ethers of activated oximes with diazoalkanes was investigated, and a simple synthesis was developed for difficultly obtainable O-substituted 1-hydroxy-2,2aziridine dicarboxylic esters. 2. The acid-catalyzed decomposition of dimethyl 1-tosyloxy-Δ2-1,2,3-triazoline-5,5dicarboxylate leads to aziridine and methyl p-toluenesulfonate. During thermolysis and direct photolysis the product from the retroprocess tosyloxyiminomalonate and its homolog tosyloxyiminosuccinate are formed in addition. The yield of the latter decreases during sensitized photolysis. 3. It was found that the saponification of the alkyloxyiminomalonic esters is trans stereospecific, and the Z and E Isomers of methyl ethyl methoxyiminomalonate. were.synthesized. 4. Optically active dimethyl 1-tosyloxy-2,2-aziridinedicarboxylate was obtained by crystallization froml-methyl lactate.