Stereochemical Studies of Monoterpene Compounds. X. Intramolecular Interaction of Oxirane and Cyclopropane Rings with a Hydroxyl Group
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概要
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The intramolecular interaction of oxirane and cyclopropane rings with a hydroxyl group in the alicyclic α,β-epoxy-, β,γ-epoxy-, and cyclopropyl alcohols was investigated by means of the infrared spectroscopy. <I>cis</I>-α,β-Epoxyalcohols (II, IV and V) showed a free hydroxyl band, an interacted hydroxyl band with a C–O bond of the oxirane ring, and/or a band due to a O–H···O hydrogen bond, whereas <I>trans</I>-epoxyalcohols (I and III) showed only a free hydroxyl band. The interaction between the hydroxyl group and a C–C bond of the oxirane ring was likely to be absent. β,γ-Epoxyalcohols revealed a hydroxyl band interacting with lone-pair electrons of the oxirane oxygen, in addition to a free hydroxyl band. The O–H··· cyclopropane interaction was found with 2-(1-methylcyclopropyl)-5-methylcyclohexanols (VII and VIII). The correlation of the infrared spectra with the conformation of the interacting groups is also discussed.
- 公益社団法人 日本化学会の論文
著者
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Watanabe Satoru
Department Of Astronomy School Of Science The University Of Tokyo
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Suga Takayuki
Department Of Chemistry Facalty Of Science Hiroshima University
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Shishibori Tsuyoshi
Department of Liberal Arts and Sciences, Faculty of Health Sciences, Kagawa Prefectural College of Health Sciences/Department of Medical Technology, Faculty of Health Sciences, Kagawa Prefectural College of Health Sciences
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Matsuura Tamon
Department of Chemistry Faculty of Science Hiroshima University
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