A Silyl Substituent Dictates the Pathway of a Concerted Electrocyclic Ring-opening of Cyclobutene
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概要
- 論文の詳細を見る
The previous studies on rhodium chemistry directed us to investigate the substituent effect of silicon on an electrocyclic ring-opening reaction of cyclobutene. It was discovered that a silyl substituent accelerates the reaction and prefers inward rotation, giving the Z-isomer. These intriguing effects were explained by the electron-accepting interactions between the low-lying σ<SUP>*</SUP> orbital of the silicon atom and the HOMO orbital of the opening cyclobutene system, possible only in the inward transition state. On the basis of this finding, a novel method for the stereoselective synthesis of functionalized 1, 3-butadiene derivatives from cyclobutenones was developed.
- 社団法人 有機合成化学協会の論文
- 2002-11-01
著者
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Ito Yoshihiko
Department Of Mathematics Faculty Of Education Kumamoto University
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Ito Yoshihiko
Department Of Synthetic Chemistry And Biological Chemistry Graduate School Of Engineering Kyoto Univ
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Murakami Masahiro
Department Of Synthetic Chemistry And Biological Chemistry Graduate School Of Engineering Kyoto Univ
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Murakami Masahiro
Department Of Aquatic Bioscience Graduate School Of Agricultural And Life Sciences The University Of
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MIYAMOTO Yasufumi
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto Un
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Miyamoto Yasufumi
Department Of Synthetic Chemistry And Biological Chemistry Graduate School Of Engineering Kyoto Univ
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MURAKAMI Masahiro
Department of Anatomy, Kurume University School of Medicine
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