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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概要

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• 1,3-Dipoles, such as phenylglyoxylonitrile oxide (<B>1</B>), benzonitrile oxide, and phenyl azide, undergo cycloadditions to the more electron-rich double bond of 2,3-bis(methoxycarbonyl)bicyclo[2.2.2]octa-2,5-diene (<B>5</B>) to afford only <I>endo</I> adducts. The cycloadditions of these 1,3-dipoles to the more electron-rich double bond of 6,7-bis(methoxycarbonyl)bicyclo[3.2.2]nona-6,8-diene (<B>6</B>) give only <I>exo</I> adducts. Benzonitrile-<I>N</I>-phenylimine (<B>4</B>) undergoes cycloadditions to both the more electron-rich and the more electron-poor double bonds of <B>5</B> or <B>6</B>. The reaction of <B>4</B> with <B>5</B> yields two endo adducts, and the reaction of <B>4</B> with <B>6</B> gives two <I>exo</I> adducts. However, the cycloaddition of <B>1</B> to 5,6-<I>endo</I>,<I>endo</I>-bis(methoxycarbonyl)bicyclo[2.2.2]oct-2-ene affords both the <I>exo</I>- and <I>endo</I> adducts. The reason for the predominant endo cycloadditions toward <B>5</B> and <I>exo</I> cycloadditions toward <B>6</B> is discussed.

• 公益社団法人 日本化学会の論文

著者

• Taniguchi Hisaji

  Department Of Applied Chemistry Graduate School Of Engineering Osaka Prefecture University

• Imoto Eiji

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

• Ikeda Toshikazu

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

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