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Teoret. i eksperim. khimiya. 2006. Vol.42 No. 1. p. 14-18

Kinetics, Selectivity and Mechanism of Reactions of Arenes
with Adamantyl Carbocations in Sulfuric Acid

 

L. K. Volkova, E. S. Rudakov


L. M. Litvinenko Institute of Physical-Organic and Coal Chemistry, National Academy of Sciences of Ukraine
Vul. R. Luxemburg 70, 83114 Donetsk, Ukraine. E-mail: rudakov@skif.net


The data on the kinetics, selectivity, KIE and the effect of the medium acidity on the rate of reactions of benzene and alkylbenzenes in sulfuric acid (59-78 mass % H2SO4) solutions of 1-adamantanol at 30 oC testify about adamantyl (Ad+) carbocations are straightforward reagent, alkylating arenes; orto-position of benzene ring are not accessible because of steric hindrances; attack rate by Ad+ cation accessible para- and meta-positions of ring is controlled by formation of σ-complex.


Key word 1-adamantanol, adamantyl cations, sulfuric acid, arene, alkylation, kinetics, substrate selectivity, mecha-
nism, steric hindrances.