Y. Sugahara, J. Hayami, A. Sera
Sep 1, 1969
Citations
0
Influential Citations
2
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The destructive alkylation reaction of benzene with 3-methylpentane to give ethylbenzene in the presence of aluminum chloride was investigated. When 3-methylpentane-1-14C was employed, radioactive ethylbenzene was obtained. A radioassay of radioactive ethylbenzene showed that: a) the specific radioactivity of the ethylbenzene was about one-third that of the starting 3-methylpentane-1-14C, and b) more than 90% of the radioactivity of the ethylbenzene was present on the β-carbon atom of the ethyl group. These findings suggested a preceding equilibrium between 3-methylpentane and 2-methylpentane, which resulted in an equivalent localization of the radioactive label on three methyl groups of these C6-hydrocarbons. A carbonium-ion mechanism including an intermediate ethyl cation was discussed in detail.