The irradiation of an optically pure isomer of a spirooxaziridine, (2f?,o'5')-6(e)-reri-butyl-2-(a:-methylbenzyl)l,2-oxazaspiro[2.5.]octane, gave a single lactam, (5S,aS)-5-/ert-butyl-l-(a:-methylbenzyl)hexahydro-2-azepinone. The absolute configurations of these two compounds were established by chemical methods and X-ray crystal structure analysis. The comparison between the configurations of the reactant and product leads to the conclusion that the C-C bond cleaved is the bond in the anti position with respect to the lone pair of the oxaziridine nitrogen atom. This work provides clear evidence in support of

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R e~u le 30 mai 1966The ozonolysis of indene in ethanol yields 3-hydroxy-4,5-benzo-7-ethoxy-l,2-dioxacycloheptane and 3-ethoxy-4,5-benzo-7-hydroxy-l,2-dioxacycloheptane, roughly in a 1:l ratio, thus showing that the cleavage of the primary indene ozonide follows the two possible courses: For personal use only.