The principal reactions of cyclohexene under the conditions studied were (1) isomerization, (2) polymerization and (3) hydrogen transfer. The hydrogen transfer was primarily from the polymer resulting in the formation of dimethylnaphthalenes and the hydrogenation of the methylcyclopentenes to methylcyclopentane.Naphthalene was the product formed most abundantly from tetralin. Scission of the hydroaromatic ring gave benzene, toluene, xylenes, possibly ethylbenzene, and higher boiling alkylated benzenes. No alkenylbenzenes were isolated. They may have been formed and then converted into the corresponding alkyl derivatives by hydrogen made available by the conversion of tetralin to naphthalene. Some of the tetralin was converted to bicvcloparaffins, presumably decalin or its isomers. The products can be explained by reactions of (1) scission of the hydroaromatic ring and (2) hydrogen transfer. Apparently, isomerization also occurred, for the xylene fraction contained xylenes other than o-xylene.The chief products formed from decalin were "isodecalins," C3 and C< olefinic and paraffinic gases in which isobutane predominated, methylcyclopentane, and probably cyclohexane and the corresponding olefins. In addition, tetralin or its isomers was found and the aromatic reaction products of tetralin conversion indicated above. The products can be explained by the following reactions of decalin and the intermediate tetralin:(1) isomerization, (2) ring scission and (3) hydrogen transfer.Chicago, III.

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Vol. 60 the other in the intermediate ion. This may occur intramolecularly or with the aid of the solvent; the present data give no means of distinguishing between the two. A similar problem has arisen previously in the mechanism of acetone exchange, which is both general acid and hydroxyl ion catalyzed.6 Summary 1. From experiments demonstrating that benzil exchanges with heavy oxygen water much more rapidly in alkaline than in neutral solution, it is concluded that the first step in the benzilic acid rearrangement is a rapid, reversible addition of hydroxyl ion to benzil, the rate-controlling step being rearrangement of the ion thus formed.2. This mechanism is entirely consistent with organic evidence and with the theory of reactivity of organic compounds as a function of electron displacements developed by English workers.New York, N. Y.

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