T. Hasegawa, K. Mukai, Kimiko Mizukoshi
Nov 1, 1990
Citations
0
Influential Citations
17
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
2-(Dibenzylamino)ethyl 4-phenyl-3-oxobutanoate underwent photocyclization via remote hydrogen migration to give 9-membered azalactones, while 2-(dimethylamino)ethyl 4-phenyl-3-oxobutanoate gave only a polymer. Irradiation of 2-(N-methylbenzylamino)ethyl 4-phenyl-3-oxobutanoate gave azalactones via a benzylic hydrogen transfer. No azalactones via methyl hydrogen migration could be detected. The stability and conformational flexibility of biradical intermediates are important factors in the present photocyclization.