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Catalytic Hydrogenolysis of Halogen Compounds 261 genated to R/CH2COCH3. In no case was there reduction of the carbonyl group. However, in the previous work,2 the carbonyl groups in ArCOCHa and ArCOCH2CH2COOCH3 were almost completely reduced to methylene groups.With the primary alcohols RCH2OH, VI, and RCH2CH2OH, VII, not only was the ring smoothly dehydrogenated but the primary alcohol function was degraded by loss of one mole of hydrogen and one of carbon monoxide according to the following equations:CioH"CH3OH -> C10H8 + 3H¡ + CO CioH,iCH2CHíOH -> C10H7CH3 + 3Hi + CO

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The Preparation of Some Substituted Piperazines 263 tained pure because both were very hygroscopic. The picrate and picrolonate were obtained as well-characterized crystalline salts.Picrate.-Prepared in and recrystallized from absolute ethanol, the picrate formed yellow elongated prisms which softened at 210°and melted, with decomposition, at 218.5-219.5°(cor.).