1,3-Dipolar cycloadditions to bicyclic olefins. I. 1,3-Dipolar cycloadditions to norbornadienes.

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概要

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• The 1,3-dipolar cycloadditions of phenylglyoxylonitrile oxide, benzonitrile-<I>N</I>-phenylimine, or <I>N</I>-phenyl-<I>C</I>-<I>p</I>-nitrophenylnitrone to norbornadiene, 2,3-dicyanonorbornadiene, and 2,3-bis(methoxycarbonyl)norbornadiene give the <I>endo</I>-adducts, together with the <I>exo</I>-adducts. These findings show that the 1,3-dipolar cycloadditions to norbornadienes do not follow the "<I>exo</I> rule." It is suggested that the present 1,3-dipolar cycloadditions are kinetically controlled reactions. The <I>endo</I>-side of norbornadienes is found to be homoconjugated by their NMR spectra. The homoconjugation must be responsible for the observed phenomenon.

• 公益社団法人 日本化学会の論文

著者

• Ikeda Toshikazu

  Department of Applied Chemistry, College of Engineering, University of Osaka Prefecture

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• 1,3-Dipolar cycloadditions to bicyclic olefins. I. 1,3-Dipolar cycloadditions to norbornadienes.
• 1,3-Dipolar cycloadditions to bicyclic olefins. IV. The influence of non-neighboring double bonds on the stereoselectivity in 1,3-dipolar cycloadditions to bicyclo[n.2.2]alkadienes.

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