Photo-oxygenation of 1H-1,2-diazepine and azepine derivatives: Formation and some reactions of their epidioxides.

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The photo-sensitized oxygenation of 1, 2-diazepines (1 and 12) and azepine (17) results in the formation of the corresponding relatively stable epidioxides (2, 13, and 18). The dioxides (2) react with potassium hydroxide to give the epoxy-ketones (10) and with methanol to give the solvent adducts (11), probably via the intermediates (8 and 9). Treatment of 13 with alumina gives the hydroxy-epoxide (15), which is converted to the epoxy-diazepinone (16) by an alkali treatment. However, a similar treatment of 18 with bases gives only N-ethoxycarbonylaniline (19) and does not give any other characterized products.

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