Journal of the Chemical Society. Perkin transactions II p. 1039 - 1042 (1987)
Update date:2022-08-05
Topics:
Armesto, Diego
Horspool, William M.
Langa, Fernando
Perez-Ossorio, Rafael
The u.v. irradiation of several 1-aryl derivatives of 3,3-dimethyl-5,5-diphenyl-1-azapenta-1,4-diene has been carried out.All of them undergo the aza-di-?-methane rearrangement and yield a cyclopropylimine.The influence of substituents on the 1-aryl group has given support for the proposal that imines with a low ionization potential are less efficient at undergoing the aza-di-?-methane process than imines with a higher ionization potential.This was demonstrated in a quantitative fashion.The involvement of an electron-transfer process in the reaction is discussed.
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