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The disproportionation of ethylbenzene-1-C141 under the influence of aluminum bromide and hydrogen bromide

✍ Scribed by Envare Ünseren; Alfred P. Wolf

Publisher
Elsevier Science
Year
1961
Tongue
French
Weight
195 KB
Volume
2
Category
Article
ISSN
0040-4039

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✦ Synopsis

It is known3 that the disproportionation4 of ethylbenzene to give benzene and a mixture of di-and triethylbenzenes catalyzed by hydrogen bromide promoted aluminum bromide is much faster than the corresponding disproportionation of toluene. McCaulay and Lien3 have explained the huge rate difference on the basis of hyperconjugative stabilization of the transition state in the case of ethylbenzene. Brown and Smoot5 modified this mechanism by suggesting that the first formed sigma complex rapidly isomerized to a nromplex, which complex was in mobile equilibrium with the starting material. Thus according to this concept, the rate determining step involving two molecules of alkyl benzene depends on the concentration of this n-complex which could reasonably be expected to be significantly higher than the corresponding nmlex derived from toluene.

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