Molecular structures of diarylcyclobutanes associated with reactivities in ring-cleavage reactions: Implications of conformationally controlled through-bond coupling.
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概要
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Molecular structures of diarylcyclobutanes (<B>1–6</B>) have been determined by single-crystal X-ray analyses. Although the distances and angles of the cyclobutane rings are relatively normal, the torsional angles between the aryl ring and the plane involving the ipso carbon and the aryl-substituted carbons of cyclobutane ring are close to 90° in cases of <B>1–4</B>, but very small (2.3–11.3°) in cases of <B>5</B> and <B>6</B>; conformations of the aryl substituents are highly restricted by the rigid tricyclic structure or by nonbonding interactions between the vicinal substituents in the cis configuration. Restricted conformations are closely related to the different reactivities of the cyclobutane in photochemical, thermal, and radiation-induced ring-splitting reactions. The structure-reactivity relationships are discussed in terms of the conformation-controlled π–σ orbital interactions associated with the capabilities of the π electron systems in through-bond coupling.
- 公益社団法人 日本化学会の論文
著者
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Shima Kensuke
Department Of Applied Chemistry Faculty Of Engineering Miyazaki University
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Imada Kiyohisa
Department Of Applied Chemistry Faculty Of Engineering Miyazaki University
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PAC Chyongjin
Department of Chemistry, Toho University
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Kimura Jun
Department Of Gastroenterology Ogaki Municipal Hospital
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YASUDA Masahide
Depariment of Hygienic Chemistry, Osaka College of Pharmacy
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Imada Kiyohisa
Department of Industrial Chemistry, Faculty of Engineering, Miyazaki University
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Yoshida Kouhei
Department of Industrial Chemistry, Faculty of Engineering, Miyazaki University
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Yasuda Masahide
Department of Industrial Chemistry, Faculty of Engineering, Miyazaki University
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Pac Chyongjin
Department of Chemical Process Engineering, Faculty of Engineering, Osaka University
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