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Photochemical Reactions of β,γ-Unsaturated Aromatic Amines by Y. Ogata; K. Takagi is a Chemistry article available to read on EtoBox.

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## Atid -Exposure of a dilute solution of N-allylanihne (1) in EtOH to UV light under Nx gave mainly aniline (57%). accompanied by o-allylaniline (2. 6.8%) and pallylanilinc (3, 11.70/,) etc. Irradiation of 1 in the presence of an oxidising agent such as FeCI,.6H,O gave ditferent products. quinoline (4) in a low yield (2.6%). together with benzene. aniline and an unknown product. No reaction of I with FeCI,\*6H,O to yield 4 occurred in the dark at room temperature. Similarly, N-allyl-a-naphthylamine (5) is photooxidisad with FeCI,\*6H,O to benxo[h]quinoline (6. 2.4%). Further, irradiation of N-cinnamylanihne (8) in the presence of an oxidising agent gave 2-phenylquinoline (9. 5%) instead of the expected Qphenylquinoline (10). The 2-phenyl isomer (9). but not 10. was obtained in a good yield on photolysis of N-cinnamylideneaniline (11). which is expected in the FeCI,\*6H,O oxidation of 8. Robable reaction pathways are discussed. UV IRRADIATION of N-alkylanilines gives mainly o-and p-alkylanilines.' The acidcatalysed rearrangement of N-alkylanilines in the dark, known as the Hofmann-Martius reaction. proceeds via an intermolecular attack of alkyl carbonium ion to phenyl carbon3 On th

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Author

Y. Ogata; K. Takagi

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1971

Language

EN

Field

Chemistry (Physical Sciences)