Studies of Organic Catalytic Reactions. IV. A Redox Reaction between Unsaturated Organic Compounds and Primary Alcohols in the Presence of Nickel Catalysts

Abstract

Abstract Styrene, mesityl oxide, benzonitrile and nitrobenzene are reduced when heated with primary alcohols, such as methanol, ethanol, 1-butanol and benzyl alcohol, in the presence of nickel catalysts. On the other hand, aldehydes are obtained by the dehydrogenation of the primary alcohols. The relative reactivity of the functional groups for the reduction is as follows: C=C>C≡N>NO2>C=O. The carbonyl group and the benzene nucleus can not be reduced under these reaction conditions. A selective reduction occurs in the reaction with mesityl oxide. The lower limit of the reaction temperature depends on the combination of the two species of the hydrogen donor (primary alcohol) and the acceptor compounds. The use of a large excess of alcohols for the reduction is effective in this redox reaction. In the reaction between styrene and benzyl alcohol, the ratio of the decreased amount of styrene to the increased amount of ethylbenzene is always 1 : 1, as determined by gas chromatographic analysis.