Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
We performed quantum-chemical AM1 modelling of the Diels-Alder heteroreaction of 1-phenylbut-2-ene-3-thione and 2-(N-pyrrolidinyl)pent-2-ene-4-thione with symmetrical dienophiles. We calculated the HOMO/LUMO energies of dienes and dienophiles as well as the activation energies of the corresponding reactions. The reaction has direct electron requirements. The principal possibility of the reaction of 2-(N-pyrrolidinyl)pent-2-ene-4-thione with electron-excessive dienophiles was outlined. Also we proved the significant difference in the reactivity of norbornene and cyclohexene dienophiles with α,β-unsaturated thiocarbonyl compounds.
unsaturated thiocarbonyl compounds, the Diels-Alder heteroreaction, thiopyranes synthesis, quantum-chemical modelling, AM1 method
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