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Intramolecular 1,3-dipolar addition reactions of nitrones were investigated. Four alkenyl nitrones were studied: 2-allyl-, 2-(3-butenyl)-, 2-(4-pentenyl)-, and 2-(9-decenyl)-N-methylcyclohexanimine N-oxides. Among these, 2-(3-butenyl)-N-methylcyclohexanimine N-oxide was found to cyclize most smoothly, giving a perhydroindene derivative as a single regio- and stereoisomer. A perhydroazulene derivative was obtained by cyclization of 2-(3-butenyl)-N-methylcycloheptanimine N-oxide.
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Takahashi et al. (1981) studied this question.
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