The Journal of organic chemistry

Orbital Unsymmetrization Affects Facial Selectivities of Diels-Alder Dienophiles

I Okamoto, T Ohwada, K Shudo

Index: Okamoto, Iwao; Ohwada, Tomohiko; Shudo, Koichi Journal of Organic Chemistry, 1996 , vol. 61, # 9 p. 3155 - 3166

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Citation Number: 23

Abstract

We investigated the Diels-Alder reactions of maleic anhydrides embedded in a dibenzobicyclo [2.2. 2] octatriene motif as a nonsterically biased dienophile. Substituents on a benzene ring in these dienophiles are far from the reaction center, providing a sterically equivalent π-face. Instead substituents can unsymmetrize the dienophilic π face through π*(anhydride)-π*(aromatic) orbital interactions. Electron-withdrawing substituents affect ...