Stereochemical and mechanistic aspects of the base-catalysed decomposition of N-alkyloxaziridines to form NH ketimines
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 867-872
- https://doi.org/10.1039/p19860000867
Abstract
The synthesis of a new range of oxaziridines (18)–(23), (30)–(35) by peracid oxidation of diaryl ketimines and aryl aldimines is reported. Relatively stable NH ketimine products (24)–(27) have been isolated from base-catalysed decomposition of the oxaziridines (18)–(20), (30)–(35) and a primary kinetic isotope effect (ca. kH/kD 6.0) was observed during decomposition of the oxaziridine trans-(31). The trans-oxaziridines (31)–(35) were found to decompose at a faster rate than the corresponding cis isomers. The relative rates of base-catalysed decomposition of oxaziridine stereoisomers are consistent with a mechanism involving an α-C–H proton abstraction mechanism.This publication has 1 reference indexed in Scilit:
- Chemistry of oxaziridines. 3. Asymmetric oxidation of organosulfur compounds using chiral 2-sulfonyloxaziridinesJournal of the American Chemical Society, 1982