1,3-Dipolar Cycloadditions to Bicyclic Olefins. I. 1,3-Dipolar Cycloadditions to Norbornadienes

The 1,3-dipolar cycloadditions of phenylglyoxylonitrile oxide, benzonitrile-N-phenylimine, or N-phenyl-C-p-nitrophenylnitrone to norbornadiene, 2,3-dicyanonorbornadiene, and 2,3-bis(methoxycarbonyl)norbornadiene give the endo-adducts, together with the exo-adducts. These findings show that the 1,3-d...

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Published inBulletin of the Chemical Society of Japan Vol. 50; no. 10; pp. 2694 - 2699
Main Authors Taniguchi, Hisaji, Ikeda, Toshikazu, Yoshida, Yoshihiro, Imoto, Eiji
Format Journal Article
LanguageEnglish
Published Tokyo The Chemical Society of Japan 01.10.1977
Chemical Society of Japan
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Summary:The 1,3-dipolar cycloadditions of phenylglyoxylonitrile oxide, benzonitrile-N-phenylimine, or N-phenyl-C-p-nitrophenylnitrone to norbornadiene, 2,3-dicyanonorbornadiene, and 2,3-bis(methoxycarbonyl)norbornadiene give the endo-adducts, together with the exo-adducts. These findings show that the 1,3-dipolar cycloadditions to norbornadienes do not follow the “exo rule.” It is suggested that the present 1,3-dipolar cycloadditions are kinetically controlled reactions. The endo-side of norbornadienes is found to be homoconjugated by their NMR spectra. The homoconjugation must be responsible for the observed phenomenon.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.50.2694