FORMATION OF A 1,2,4-DIOXAZOLIDINE BY ELECTRON-TRANSFER PHOTOOXYGENATION OF 1-BUTYL-2,3-DIPHENYLAZIRIDINE

Article abstract of DOI:10.1016/S0040-4039(00)88091-0

Electron-transfer photooxygenation of 1-butyl-2,3-diphenylaziridine with 9,10-dicyanoanthracene in oxygen-saturated acetonitrile yields 4-butyl-3,5-diphenyl-1,2,4-dioxazolidine.This peroxide is surprisingly stable in nonpolar solvents decomposing to benzaldehyde and N-butylbenzamide upon heating to 100 deg C in benzene.Treatment with triphenyl phosphine yields benzaldehyde and N-butyl-1-phenylmethanimine.