Hydrogenation and hydrogenolysis. XVI. The reactions of two isomeric enol ethers of 3-methylcyclohexanone over platinum group metals.
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概要
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The two isomeric enol ethers of 3-methylcyclohexanone, 1-ethoxy-3-methyl-, and 1-ethoxy-5-methylcyclohexenes (<B>5</B> and <B>6</B>), have been hydrogenated in ethanol with six platinum group metals as catalysts. Palladium, rhodium, and platinum efficiently catalyzed the addition of ethanol to the enol ethers to give the corresponding acetal, while iridium and ruthenium catalyzed it only slightly. Osmium was moderately active for the acetal formation. Extensive isomerization between <B>5</B> and <B>6</B> occurred over all catalysts. In addition, isomerization to an allyl ether, 3-ethoxy-1-methylcyclohexene (<B>9</B>), was observed with <B>5</B> over the metals other than palladium. Hydrogenation of <B>5</B> and <B>6</B> with palladium gave the <I>trans</I>-ether predominantly. With the other metals, the <I>cis</I>-ether was formed in large excess from <B>5</B> and the <I>trans</I>-ether in slight excess from <B>6</B> at the initial stage of hydrogenation. Hydrogenolysis of the ethoxyl group occurred extensively over platinum but only slightly with palladium and ruthenium. These results are compared with those obtained with the corresponding dimethylcyclohexenes and allyl ether <B>9</B>.
- 公益社団法人 日本化学会の論文
著者
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Nishimura Shigeo
Department Of Applid Chemistry For Resources Tokyo University Of Agriculture And Technology
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SATO NOBUO
Department of Diagnostic Radiology Cancer Institute Hospital
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Sato Nobuo
Department of Industrial Chemistry, Tokyo University of Agriculture and Technology
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Kagawa Kunihiro
Department of Industrial Chemistry, Tokyo University of Agriculture and Technology
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