Bulletin of the Chemical Society of Japan

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 …

H Taniguchi, T Ikeda, E Imoto

Index: Taniguchi,H. et al. Bulletin of the Chemical Society of Japan, 1978 , vol. 51, p. 1495 - 1500

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Citation Number: 4

Abstract

1, 3-Dipoles, such as phenylglyoxylonitrile oxide (1), 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 (5) to afford only endo 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 (6) give only exo adducts. Benzonitrile-N-phenylimine (4) undergoes ...

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