
TY  - JOUR
A1  - Bapat, JB 
A1  - Black, DS 
T1  - Nitrones and oxazirans. III. Photolysis of 1-pyrroline 1-oxides and their related oxazirans
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1968
VL  - 21
IS  - 10
SP  - 2507
EP  - 2520
KW  - 
UR  - https://doi.org/10.1071/CH9682507 
N2  - 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. 
ER  -

