trans -2-(dimethylaminomethyl)cyclohexylamine, 53369-74-7; 2-methyl-3-dimethylaminopropylamine, 6105-72-2; 4-methyl-3,4-diazatricyclo[5.2.1.02'6]-2-decene, 53369-75-8; 3-methyIene-2-norbornanone, 5597-27-3; methylhydrazine, 60-34-4; o-(dimethylammo'methyl)benzonitrile, 53369-76-9; o-cyanobenzyl bromide, 22115-41-9; dimethylamine, 124-40-3; o-(dimethylaminomethyl)benzylamine, 53369-77-0; o -(dimethylaminomethyl)benzylamine hydrochloride, 53369-78-1; , , ', ',2,2-hexameth-yI-l,3-propanediamine, 53369-79-2; o-bis(dimethylaminomethyl)benzene, 53369-80-5; o-bis(dimethylaminomethyl)benzene monoperchlorate, 53369-81-6.Miniprint Material Available. Full-sized photocopies of the miniprinted material from this paper only or microfiche (105 X 148 mm, 24X reduction, negatives) containing all the miniprinted and supplementary material for the papers in this issue may be obtained from the
DIFLUOROMETHYLENE IN THE REACTION OF CHLORODIFLUOROMETHANE 5493 temperature was kept under 35' by external cooling. When the reaction became sluggish, more catalyst was added. Reduction was complete when a viscous yellow oil appeared and only a faint odor of nitrobenzene could be detected." Water was added and the mixture placed in an icesalt-bath. The yellow oil soon crystallized. The crude azoxybenzene was removed by rapid filtration. Some of the impurities oiled out leaving behind a yellow solid. The oil was chilled and the process repeated for an additional yield of crude azobenzene. The azoxybenzene was recrystallized from alcohol, yield 5.5 g. (6570), m.p.
34-35:.On a second recrystallization the product melted a t 35-36 .2,2'-Dimethy1azoxybenzene.-To 10 g. of o-nitrotoluene (0.073 mole) was added 9 ml. of lOOYo hydrazine hydrate (0.18 mole) and 20 ml. of 95% ethanol. Some Raney nickel catalyst was introduced. There was much effervescence and the mixture turned slightly green, then yellow. The temperature of the reaction was kept under 35". When the reaction became less vigorous, the solution was orange. More catalyst was added and the mixture allowed to stand a t 0" overnight. The resulting orange-yellow crystals of 2,2'-dimethylazoxybenzene were collected by filtration and recrystallized from a mixture of alcohol and water. A second crop was obtained by adding water to the mother liquor, from the original filtration and treating the resulting dark orange-red oil with dil. HC1 until it crystallized. The total yield was 3.2 g. (39%), m.p. 57.5-58.5".18 4,4'-Dimethy1azoxybenzene.-Ten grams of p-nitrotoluene (0.073 mole) was suspended in a solution of 9 ml. of 1 0 0~o hydrazine hydrate (0.18 mole) and 30 mi. of 9570 ethanol. Some Raney nickel catalyst was introduced and the mixture stirred for several hours. The p-nitrotoluene gradually dissolved and yellow crystals of 4,4'-dimethylazoxybenzene were deposited. When effervescence had ceased, the product was filtered and recrystallized from a mixture of alcohol and water. This yield was 3.4 g. (427,), m.p. 7O-7l0.l8
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