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D. N. Mityagin, I. M. Gabbasova, A. V. Anisimov, E. A. Kantor
Mechanism for moving of the C=C bond
migration allylphenylsulfide catalyzed by methanesulfonic acid
Abstract
Quantumochemically, using the density
functional theory in the B3PW91/6-31G** approximation the mechanism of C=C bond
displacement in allylphenylsulfide in the presence of methanesulfonic acid was
analyzed. The reaction proceeds through the formation of
1-(phenylthio)prop-2-yl or 2-methyl-1-phenyl-thiirany. The calculations show
the possibility of the protonation reaction of allylphenylsulfide proceeding
and the deprotonation of the resulting cation to propenylphenylsulphide, as
well as the opening of the thiranium cation under the action of methylsulfonate
to form the propenylphenylsulfide complex with methanesulfonic acid. Comparison
of the calculation results without solvent and with its account, shows that the
profile of the potential energy of the reaction is practically preserved.
Key words: quantum-chemical calculations,
transition state, allylphenilsulfide, propenylphenilsulfide, tiiranium cation.
Copyright (C) Chemistry Dept., Moscow State University, 2002
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