
%0 Journal Article
%A Glover, SA 
%A Hammond, GP 
%A Harman, DG 
%A Mills, JG 
%A Rowbottom, CA 
%T Cyclization of Alkoxyiminyl Radicals Onto Olefins: Formation of 2-Alkoxy-Delta(1)-Pyrrolines, 4,5-Dihydrooxazoles and 5,6-Dihydrol-4h-1,3-Oxazines
%J Australian Journal of Chemistry
%D 1993/08/01
%V 46
%N 8
%P 1213-1228
%K 
%R https://doi.org/10.1071/CH9931213
%U https://www.publish.csiro.au/paper/CH9931213 
%X Alkoxyiminyl  radicals, generated by photolysis of N-bromo imidates, undergo exo-1,5 and exo-1,6 cyclization onto olefins on the O-alkyl side chains giving good yields of 4,5-dihydrooxazoles and 5,6-dihydro-4H-1,3-oxazines, respectively. exo-1,5 Cyclization onto an olefin on the iminyl side chain gives 2-alkoxy-&#916;1-pyrrolines. 4,5-Dihydrooxazole formation is more favourable than cyclization to 2-alkoxy-&#916;1-pyrrolines and both reactions are irreversible. These preferences are supported by MNDO molecular orbital calculations which predict that both processes are exothermic but cyclization onto the O- alkenyl side chain has a lower &#916;H&#8225;. 
