
TY  - JOUR
A1  - Glover, SA 
A1  - Hammond, GP 
A1  - Harman, DG 
A1  - Mills, JG 
A1  - Rowbottom, CA 
T1  - Cyclization of Alkoxyiminyl Radicals Onto Olefins: Formation of 2-Alkoxy-Delta(1)-Pyrrolines, 4,5-Dihydrooxazoles and 5,6-Dihydrol-4h-1,3-Oxazines
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1993
VL  - 46
IS  - 8
SP  - 1213
EP  - 1228
KW  - 
UR  - https://doi.org/10.1071/CH9931213 
N2  - 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;. 
ER  -

