S. Wake, Yuichi Takayama, Y. Otsuji
May 1, 1974
Citations
0
Influential Citations
12
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Irradiation of phthalazine (1) and quinoxaline (2) in acidified methanol yielded 1-methylphthalazine (3a) and 2-methylquinoxaline (4), respectively. The quantum yields for the formation of 1-alkylphthalazines, which were obtained upon irradiation of 1 in acidified alcohols, varied with the sort of alcohols used and decreased in the order of methanol>ethanol>>2-propanol. When a mixture of 1 and 2,6-di-t-butylphenol (6) was irradiated in benzene containing trifluoroacetic acid under evacuated conditions, the oxidation of 6 occurred to form 3,5,3′,5′-tetra-t-butyldiphenoquinone (7) without destruction of 1. Detailed mechanistic studies suggest that the photoalkylations of 1 and 2 in acidified alcohols proceed through an electron-transfer from solvents to an excited state of the protonated diazines.