Abstract
The photolysis of 6-cyanophenanthridine 5-oxide (1) in various solvents was reported. In addition to the expected 6-cyanodibenz [d, f] [1, 3] oxazepine (2), two new types of rearrangement products : 5-alkoxyphenanthridin-6 (5H)-one (3), as a byproduct in the photolyses using an aprotic solvent, were obtained in the present experiments. In order to account for the formation of these products (3 and 9), reasonable assumptions that the oxygen walk process from the oxaziridine species (11) leading to the oxazepine (2) is relatively inhibited to occur and thus 11 has a longer life time as compared to the related oxaziridines derived from α-cyanated bicyclic amine N-oxides were proposed. A mechanistic rationalization and characteristic features in the photochemical rearrangement reactions of 1 are discussed in detail, together with the structure determinations of the photoproducts.
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