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Communication | Regular issue | Vol 4, No. 6, 1976, pp.1095-1100
Published online, 1st January, 1970
DOI: 10.3987/R-1976-06-1095
Intra- and Inter-molecular Photoreactions of N-Chloroacetyl Derivatives of Dimethylaminophenethylamines and Dimethylaminobenzylamines in Both Acidic and Basic Solutions

Naganori Numao and Osamu Yonemitsu*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

Abstract

Photocyclization of N-chloroacetyl derivatives of dimethylaminophenethylamines and dimethylaminobenzylamines were examined. Intramolecular photoreactions little affected by acid gave azepinones (V, VI) and a cage compound (VIII), while novel diazametacyclophanes (IX, XII) were obtained intermolecularly, which was strongly depressed by acid. These results suggest that the photoreactions involve the singlet excited state of the dimethylaniline moiety.