Orbital Unsymmetrization of Olefins Arising from Non-equivalent Orbital Interactions. σ-π Coupling in Bicyclo[2.2.2]octenes
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概要
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We characterized experimentally the substituent effect of a 5-exo substituent on the π facial selectivities of bicyclo[2.2.2]octenes toward electrophilic oxidative reactions such as epoxidation and dihydroxylation, and we discuss the underlying orbital interactions of vicinal σ orbitals and the olefinic π orbital involved in bicyclo[2.2.2]octenes, and commonly in methylenenorbornanes. Of significance is the out-of-phase motif of these σ-π couplings. Electron-withdrawing substituents such as cyano and carboxylic acid groups unequalize the relevant σ-π coupling, leading to the observed syn-facial preference. Alkyl substituents exhibit an electron-donative perturbing effect, depending on the bicyclic ring system.
- 公益社団法人日本薬学会の論文
- 1996-02-15
著者
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SHUDO Koichi
Faculty of Pharmaceutical Sciences, The University of Tokyo
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Okamoto Iwao
Faculty Of Pharmaceutical Sciences University Of Tokyo
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Shudo Koichi
Faculty Of Pharmaceutical Science Kyushu University
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OHWADA Tomohiko
Faculty of Pharmaceutical Sciences, University of Tokyo
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UCHIYAMA Masanobu
Faculty of Pharmaceutical Sciences, University of Tokyo
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TSUJI Motonori
Faculty of Pharmaceutical Sciences, University of Tokyo
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Tsuji Motonori
Faculty Of Pharmaceutical Sciences University Of Tokyo
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Ohwada Tomohiko
Faculty Of Phamaceutical Sciences The University Of Tokyo
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Uchiyama Masanobu
Faculty Of Pharmaceutical Sciences University Of Tokyo
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