
%0 Journal Article
%A Bapat, JB 
%A Black, DS 
%T Nitrones and oxazirans. III. Photolysis of 1-pyrroline 1-oxides and their related oxazirans
%J Australian Journal of Chemistry
%D 1968/10/01
%V 21
%N 10
%P 2507-2520
%K 
%R https://doi.org/10.1071/CH9682507
%U https://www.publish.csiro.au/paper/CH9682507 
%X Oxazirans have been prepared from a number of 1-pyrroline 1-oxides by   photoisomerization and from the related 1-pyrrolines by oxidation with perbenzoic acid. This oxidation was found to be highly stereoselective in reaction with unsymmetrical pyrrolines, and 3,5-cis-disubstituted oxazirans were formed exclusively. A mixture of 3,5-cis- and trans-disubstituted oxazirans was formed in the photolysis of unsymmetrical 2-methyl-substituted pyrroline 1-oxides but stereo-selectivity was observed in the photolysis of similar 2-aryl-substituted pyrroline 1-oxides, in which cases only the trans-isomer was obtained.   Photoisomerization of cis-5-phenyl-substituted oxazirans to their trans-isomers was also observed, while other oxazirans were found to be photo-stable. 
