ORBITAL DISTORTION IN DIBENZOBICYCLO[2.2.2]OCTATRIENES. BIASED EPOXIDATION AND DIHYDROXYLATION OF THE OLEFIN MOIETY
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概要
- 論文の詳細を見る
Epoxidation and dihydroxylation of the olefin moiety of 2-substituted dibenzobicyclo[2.2.2] octatrienes were investigated. These reactions exhibited substituent effect : 2-nitodibenzo bicyclo[2.2.2]octatriene gave predominantly the syn-epoxide and the syn-diol, with a diastereomeric excess of 54% to 76%. respectively. On the other hand, the 2-methoxy substrate showed only a small preference in the reactions, giving a slight excess of the antiproducts. This effect can be interpreted in terms of the perturbation of the occupied π orbital of the ethylene moiety arising from the mixing of the π orbitals (in particular, the HOMO) of convex-substituted dihydroxyanthracene, wherein the σ type overlaps are involved in a manner similar to the longicyclic conjugation.
- 公益社団法人日本薬学会の論文
- 1992-12-25
著者
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首藤 紘一
Faculty of Pharmaceutical Sciences, University of Tokyo
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首藤 紘一
Facutly Of Pharmaceutical Sciences University Of Tokyo
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大和田 智彦
東大 薬
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岡本 巌
Faculty Of Pharmaceutical Sciences University Of Tokyo
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芳賀 直樹
Faculty of Pharmaceutical Sciences, University of Tokyo
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大和田 智彦
Faculty of Pharmaceutical Sciences, University of Tokyo
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首藤 紘一
東京大・薬学
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大和田 智彦
Faculty Of Pharmaceutical Sciences University Of Tokyo
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芳賀 直樹
Faculty Of Pharmaceutical Sciences University Of Tokyo
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