S. Mitsui, Y. Senda, H. Saito
Apr 1, 1966
Citations
0
Influential Citations
29
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
2-Cyclopentylidenecyclopentanol (I) was hydrogenated over Raney Ni to produce a mixture of 95% of trans- and 5% of cis-2-cyclopentylcyclopentanol (III). However, over a Pd catalyst I gave a mixture of 2-cyclopentylcyclopentanone (IV), cyclopentylcyclopentane (V) and trans-and cis-III. In the hydrogenation of I over PtO2, trans-III was a predominant product (93%) in ethanol, whereas in acetic acid a mixture of 2 parts of trans- and 1 part of cis-III was obtained, and in acetic acid with one drop of hydrochloric acid, the ratio of trans and cis was one to two. A large amount of V was also obtained in cases of both acetic acid. The hydrogenation of 2-benzylidene-1-tetralol (II) resulted in 2-benzyl-1-tetralols (VI), the yields of trans- and cis-VI being as follows: over Raney Ni, 78% and 19%; over Pd, 33% and 63%; and over PtO2 in ethanol, 58% and 34%, respectively. From these results, it was found that, in the cases of Raney Ni and PtO2 in ethanol, the directive effect of the hydroxyl group is very efficien...