Isoxylitones関連化合物の接触水素添加について

概要

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E and Z forms of (3, 5, 5-trimethyl-2-cyclohexene-1-ylidene)-acetonitrile (10), (3-methyl-2-cyclohexene-1-ylidene)-acetonitrile (8) and 1-(3-methyl-2-cyclohexene-1-ylidene)-2-propanone (1) were hydrogenated over 5% Pd/C catalyst in ethanol. 8 and 1 gave both cis and trans isomers of tetrahydro compound [7 cis and trans (42:58) and 2 cis and trans (50:50) respectively]. As described in the previous report, isoxylitone [1-(3, 5, 5-trimethyl-2-cyclohexene-1-ylidene)-2-propa-none)] (1) was catalytically hydrogenated to give exclusively the cis-tetrahydro compound (2czs), whereas 10 gave the isomeric dihydro compounds [(3, 5, 5-trimethylcyclohexene-1-ylidene)-acetonitrile] (5) and the hydrogenation proceeded no further. The effect of gem-dimethyl group on the catalytic hydrogenation is discussed.
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