Cage Effect for the Photochemical Formation of the Ten-Membered Lactam from N-Chloroacetyl-3-methoxyphenethylamine

抄録

Photocyclization of N-chloroacetyl-3-methoxyphenethylamine (I) in water gave 7- and 9-methoxy-1, 2, 4, 5-tetrahydro-3H-3-benzazepin-2-ones (V and VI), whereas in organic solvents the main products changed to N-acetyl-3-methoxyphenethylamine (XVII) and 2-oxa-6-azabicyclo [7, 3, 1] trideca-1 (13), 9, 11-trien-5-one (XIII). Quantum yield for the formation of V and VI is clearly dependent on the polarity of solvent indicating that the formation of V and VI involves an ionic process. In organic solvents, viscous media favor the formation of XIII. Viscosity dependence in some alcohols is probably an indication of a novel cage reaction operative in the formation of the lactam XIII.