1954 年 74 巻 10 号 p. 1037-1039
There has been no incidence of the reduction of organic compounds with lithium amalgam and, therefore, such reduction with 1% lithium amalgam was carried out on various organic compounds. For example, reduction of carbon-carbon double bond was effected on cinnamic acid and cinnamaldehyde, yielding dihydrocinnamic acid and cinnamic alcohol. Acetophenone, as an example of carbonyl compounds, chiefly yielded a pinacone compound by this reduction, while acetone was recovered unchanged. As the nitrogenous compounds, oxime, azobenzene, and Schiff base yielded the corresponding amine, hydrazobenzene, and secondary amine, while nitriles were recovered unchanged. Reduction of nitrobenzene yielded aniline and azobenzene. It may be concluded that the activity of lithium amalgam is not different from sodium amalgam although the reaction of the former is much milder and it is interesting to note that nitriles are not reduced and ketones are comparatively indifferent to reduction.