The reduction of carbonyl compounds by means of hydrogen sulfide under pressure under the presence of MoS3 was investigated. Benzil, benzophenone and 9-fluorenone were reduced to the corresponding hydrocarbons, and sulfur-containing materials were scarcely produced. These reactions were promoted by the addition of such catalyst as p-toluene-sulfonic acid. In the case of benzaldehyde, however, the main product was benzylmercaptane and a very small amount of toluene was obtained. In the reaction of a carbonyl compound which has a hydrogen atom on the α-position of the carbonyl group, a sulfur-containing condensation material was produced as the main product.
Cis-and trans-2-vinyl-6, 6-dimethylnorpinanes, (3) and (3'), of high isomeric purity (96%) were obtained in 47 and 71% yields, respectively, by the Wittig reactions of methylenetriphenylphosphorane with cis-and trans-myrtanals, and their physical properties were characterized. The catalytic dehydration of 10-methylmyrtanols, (5) and/or (5'), over thorium oxide at ca. 370°C gave (3) and/or (3') in ca. 60% yield, together with a small amount of dehydrogenated by-products.