Stereochemical Studies of Monoterpene Compounds. XIII. The Conformational Analysis of the Acetyl Group of 4-Methyl-10-nor-8-oxomenthols by Circular Dichroism
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概要
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The conformational analysis of the acetyl group of a stereoisomeric pair of 4-methyl-10-nor-8-oxomenthols was made by means of the temperature-dependent circular dichroism. (1R:3S:4R)-(+)-4-Methyl-10-nor-8-oxoneomenthol (<B>1</B>) exhibited a double-humped Cotton effect at a low temperature. This phenomenon seems to indicate the existence of a conformational equilibrium among <B>1b</B>, <B>1c</B>, and <B>1d</B>, but not <B>1a</B>. On the other hand (1R:3R:4R)-(−)-4-methyl-10-nor-8-oxomenthol (<B>3</B>) exhibited an inversion in the sign of the Cotton effect when the solvent and the temperature were changed. This phenomenon was interpreted in terms of the conformational equilibrium among <B>3a</B>, <B>3b</B>, and <B>3c</B>. These phenomena were 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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