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PART I. THE CARBONYL GROUPSince the report by Whitman, Wintersteiner, and Schwenk (1) on the reduction of estrone to a mixture of alpha-and beta-estradiol by a nickel-aluminum (Raney) alloy in alkaline solution there has appeared in the literature, as far as we could determine, but one instance (2) of the use of this reduction method. During the course of other investigations, we have had the opportunity to study further the reducing action of this alloy. This first paper represents the results we have obtained with compounds containing the carbonyl group.Compounds of this type usually take up hydrogen quite easily when treated with nascent hydrogen, or with hydrogen in the presence of a catalyst, to give the corresponding alcohols. Occasionally, even reduction to the hydrocarbon has been observed. A more general method of obtaining the hydrocarbon is by the Clemmensen reduction, which, however, has not always given satisfactory results (3, 4). Alternative methods for accomplishing the transformation of carbonyl compounds to the hydrocarbons are the Wolff -Kishner reduction and catalytic hydrogenation.We have found that with many carbonyl compounds our reduction method gives results comparable to those obtainable by the Clemmensen reduction. However, unlike the Clemmensen reduction, our reduction method is not specific, in that it converts carbonyl compounds to either the corresponding carbinol or the hydrocarbon, the extent of the reduction depending solely on the structure of the carbonyl compound. Carbonyl compounds of the general formula I

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N,N-Diethyl-N'-(2,2-dibutylhexyl)-ethylenediamine.-A mixture of 21 g. (0.1 mole) of 2,2-dibutylhexylamine, 14 g. (0.1 mole) of diethylaminoethyl chloride and 11 g. of anhydrous sodium carbonate in 50 cc. of dry xylene was refluxed with stirring for sixty-five hours. The cooled reaction product was poured into water, the xylene layer separated, and the solvent removed in vacuo.The brown oily residue was distilled; yield 29 g.; b. p. 155-156°( 2 mm.); n23d 1.4540. The analytical sample showed the following constants:

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