Reactive intermediates. Part X. Synthesis of aziridines from aminonitrenes and olefins
- 1 January 1970
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 4,p. 576-582
- https://doi.org/10.1039/j39700000576
Abstract
Oxidation of N-aminophthalimide, 3-amino-2-methyl-4-quinazolone, and 1-amino-2-quinolone with lead tetra-acetate in the presence of a wide range of electrophilic and nucleophilic olefins is a useful, stereospecific route to aziridines. The generation and cycloaddition of singlet amino-nitrenes is proposed. Several chloro- and bromo-substituted aziridines undergo an almost quantitative, uncatalysed thermal rearrangement, with opening of the aziridine ring, to give hydrazones.Keywords
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