Quantum-chemical study of the regioselectivity of the diels-alder heteroreaction of α,β-unsaturated thiocarbonyl compounds with unsymmetrical dienophiles

Konstantin Ovchinnikov; Mihail Starostin; Nikolay Larionov

doi:doi:10.52957/27821900_2021_03_56

UDC 547.818.1

Quantum-chemical study of the regioselectivity of the diels-alder heteroreaction of α,β-unsaturated thiocarbonyl compounds with unsymmetrical dienophiles

Published в From Chemistry Towards Technology Step-By-Step · Volume 2, Issue 3, 2021 · Pages 56–60 · Rubrics: Scientific articles

DOI 10.52957/27821900_2021_03_56

Received: 06.09.2021 Accepted: 06.09.2021 Published: 23.09.2021

Authors

Konstantin Ovchinnikov ¹ · Mihail Starostin ² · Nikolay Larionov ³

1 Yaroslavl State Technical University (Associate Professor)
Yaroslavl, Yaroslavl, Russian Federation

2 Yaroslavl State Technical University
Yaroslavl, Yaroslavl, Russian Federation

3 Yaroslavl State Technical University
Yaroslavl, Yaroslavl, Russian Federation

ABSTRACT

The study considers the quantum-chemical study of the Diels-Alder heteroreaction of various substituted 3,4-dihydro-2H-thiopyrans. We study the steric and electronic factors influencing the reaction of α,β-unsaturated thiocarbonyl compounds with unsymmetrical dienophiles. We used the methods AM1, B3LYP. The analysis of calculated data for asymmetric dienophiles shows that the regioselectivity of the reaction is subject to the electron factor and can be described by the reaction activation energies, energies and localisation parameters of the boundary orbitals. The calculations are confirmed by the experimental results.

KEYWORDS

unsaturated thiocarbonyl compounds Diels-Alder heteroreaction thiopyrans quantum-chemical modelling density functional theory

Information Text

Authors:

1. Yaroslavl State Technical University (Associate Professor)

Yaroslavl, Yaroslavl, Russian Federation

2. Yaroslavl State Technical University

Yaroslavl, Yaroslavl, Russian Federation

3. Yaroslavl State Technical University

Yaroslavl, Yaroslavl, Russian Federation

Type:

Article

Pages:

from 56 to 60

Status:

Published

Subject area:

UDC 547.818.1

Language:

Russian

Keywords:

unsaturated thiocarbonyl compounds, Diels-Alder heteroreaction, thiopyrans, quantum-chemical modelling, density functional theory

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References

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