83326-62-9Relevant articles and documents
Stereochemical and Mechanistic Aspects of the Base-catalysed Decomposition of N-Alkyloxaziridines to form NH Ketimines
Boyd, Derek R.,McCombe, Kenneth M.,Sharma, Narain D.
, p. 867 - 872 (2007/10/02)
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.