Stereospecific deaminations of some N-alkylaziridines
by m-chlorobenzoic acid

H. W. Heine, J. D. Myers and E. T. Peltzer
Department of Chemistry
Bucknell University
Lewisburg, PA 17837, USA.

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.

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