Reduction of 7-Methylenebicyclo[3.3.1]nonan-3-one and Related Compounds: Structural Investigation of the Products
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概要
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Hydrogenation of 7-methylenebicyclo[3.3.1]nonan-3-one (<B>1</B>) over platinum oxide in acetic acid yielded 7α-methylbicyclo[3.3.1]nonan-3α-ol (<B>2</B>) as the sole product. Hydrogenation of (<B>1</B>) in ethyl acetate afforded 7α-methylbicyclo[3.3.1]nonan-3-one (<B>3</B>) as a reduced product and 7-methylbicyclo[3.3.1]non-6-en-3-one (<B>4</B>) as an isomerized product. Hydrogenation of <B>1</B> over palladium on carbon gave no reduced product but <B>4</B> in 100% conversion. Hydrogenation of 7-methylenebicyclo[3.3.1]nonan-3α-ol (<B>7</B>) and -3β-ol (<B>8</B>) over platinum oxide in acetic acid gave <B>2</B> and 7α-methylbicyclo[3.3.1]nonan-3β-ol (<B>5</B>), respectively. From studies based on NMR spectroscopy with use of a shift-reagent, it is concluded that the major conformer of <B>2</B> and <B>5</B> is of chair-boat form. By the equilibration experiment between <B>2</B> and <B>5</B> using aluminum isopropoxide in isopropyl alcohol at 110°C, the <I>ΔG</I><SUP>°</SUP> value was found to be −2.2 kcal/mol.
- 公益社団法人 日本化学会の論文
著者
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Kimoto Koichi
Department Of Clinical Nutrition Tokyo Kasei University
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Imagawa Takeshi
Department of Industrial Chemistry, Faculty of Engineering, Kyoto University
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Kawanisi Mituyosi
Department of Industrial Chemistry, Faculty of Engineering Kyoto University
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