Dynamic stereochemistry of imines and derivatives. Part VI. Stereochemistry of the peroxyacid–imine route to oxaziridines

Abstract

The stereochemistry of the peroxyacid oxidation of N-alkyl-aldimines and -ketimines to oxaziridines containing a stable nitrogen pyramid is considered over a range of reaction conditions. The possible relevance of reactant and product molecular geometry in distinguishing between the concerted and stepwise mechanisms is discussed. A comparison is made between rate constants of several peroxyacid oxidation reactions in different solvents. The concerted mechanism appears to be less attractive on the basis of stereochemical and solvent effect data.