Angewandte Chemie, International Edition in English (1970) 9: 374.
Received: 25 March 1970.
Published: May 1970.
When cis-1-benzyl- or cis-1-cyclohexyl-2,3-dibenzoylaziridine was treated with an equivalent quantity of m-chloroperbenzoic acid in benzene in the dark at room temperature for 24 h and the reaction mixture worked up by extracting with aqueous sodium carbonate, drying the benzene layer over anhydrous magnesium sulfate, filtering, and evaporating the benzene in the dark, 85-90% yields of a mixture of the known cis-dibenzoylethylene and the known nitroso dimer were obtained. Similar treatment of trans-1-benzyl- or trans-1-cyclohexyl-2,3-dibenzoylaziridine gave 90% yields of trans-dibenzoylethylene and nitroso dimer. The deamination reaction and the work-up of the reaction mixture must be carried out in the dark to avoid isomerization of the trans-ethylene to the cis-isomer. The stereospecific course of the reaction suggests a concerted mechanism for the deamination.
The authors thank the donors of the Petroleum Research Fund administered by the American Chemical Society for partial support of this work.