Stereochemical Studies of Monoterpene Compounds. I. The Conformation of (+)-<I>p</I>-Menthane-3,4-diol Obtained by the Performic Acid Oxidation of (+)-<I>p</I>-Menth-3-ene

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概要

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• The conformational analysis of (+)-<I>p</I>-menthane-3,4-diol, which had been obtained by the hydroxylation of (+)-<I>p</I>-menth-3-ene with performic acid in the presence of water, has been performed mainly by means of infrared spectra. It has been shown that the two hydroxyl groups at the C<SUB>3</SUB>- and C<SUB>4</SUB>-positions take a diaxial conformation, that they are, accordingly, trans to each other, and that the methyl group presumably holds an equatorial orientation. It has also been found that <I>p</I>-menthane-<I>trans</I> (diaxial)-2,3-diol results from the <I>p</I>-menth-2-ene coexisting in the sample of <I>p</I>-menth-3-ene. A stereochemical course of the hydroxylation reaction has been discussed.

• 社団法人 日本化学会の論文

著者

• Suga T.

  Department Of Dermatology Kagoshima University Faculty Of Medicine

• 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

• Matsuura Tamon

  Department of Chemistry Faculty of Science Hiroshima University

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