Stereochemical Studies of Monoterpene Compounds. XV. A Conformational Study of Carvomenthone Derivatives by Means of Temperature-dependent Circular Dichroism
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概要
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The conformations of (1<I>R</I>:4<I>R</I>)-(−)-<I>p</I>-menth-8-en-2-one (<B>1</B>) and of diastereoisomeric pairs of (+)-1-hydroxy-<I>p</I>-menth-8-en-2-one, (<B>2</B>) and (<B>3</B>), (+)-1-hydroxy-<I>p</I>-menthan-2-one, (<B>6</B>) and (<B>7</B>), and (+)-1-hydroxy-8-bromo-<I>p</I>-menthan-2-one, (<B>10</B>) and (<B>11</B>), were examined by a combination of infrared spectra and temperature-dependent circular-dichroism (CD). Explanations are given mainly with regard to the epimeric pair, (<B>2</B>) and (<B>3</B>). It is demonstrated that α-hydroxyketone (<B>2</B>) exists in a conformational equilibrium among <B>2a</B>, <B>2b</B>, and <B>2c</B>. The 2a conformer predominantly exists in a polar medium and at low temperatures, whereas the <B>2b</B> conformer is more stable than <B>2a</B> in a nonpolar medium. On the other hand, the epimer (<B>3</B>) exists preferentially in the <B>3a</B> conformation in both polar and nonpolar media and at low temperatures. The CD curves of compounds <B>6</B> and <B>7</B> exhibited the exactly same behavior as those in compounds (<B>2</B>) and (<B>3</B>) respectively. These results are interpreted in terms of the competition of the steric factor and the intramolecular hydrogen bonding.
- 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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Watanabe Satoru
Department of Chemistry, Faculty of Science, Hiroshima University
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