Bulletin of the Chemical Society of Japan p. 1777 - 1780 (1981)
Update date:2022-08-05
Topics: Ring closure Isolation and Purification Intramolecular 1,3-Dipolar Cycloaddition
Takahashi, Satoru
Kusumi, Takenori
Sato, Yoko
Inouye, Yoshinobu
Kakisawa, Hiroshi
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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