|
D. N. Mityagin, I. M. Gabbasova, A. V. Anisimov, E. A. Kantor
Quantum-chemical investigation of thermal transformations of
allylphenilsulfide
Abstract
Quantum-chemical methods for the conversion
of allyl phenyl sulfide were calculated using the density functional theory in
the B3PW91 / 6-31G** approximation. It was established that the conformation of
the chair is the probable transition state of the first stage – the conversion
of allyl phenyl sulfide to 6-(prop-2-en-1-yl)cyclohexa-2,4-diene-1-thione. The
second stage consists in the interaction of thione with the molecule of allyl
phenyl sulfide, allylthiophenol, or with the second thion molecule. Cyclization
of allylthiophenol involves the formation of methylthiocoumaran. Thermal
isomerization of allyl phenyl sulfide to propenyl phenyl sulphide is unlikely.
Key words: Claisen’s thermal rearrangement,
allylphenilsulfide, quantum chemical calculations, transition state, route of
reaction, thermal transformations.
Copyright (C) Chemistry Dept., Moscow State University, 2002
|
|
