A DFT study of 1,3-dipolar cycloaddition reactions of 5-membered cyclic nitrones with α,β-unsaturated lactones and with cyclic vinyl ethers. Part I - Archive ouverte HAL
Article Dans Une Revue Tetrahedron: Asymmetry Année : 2008

A DFT study of 1,3-dipolar cycloaddition reactions of 5-membered cyclic nitrones with α,β-unsaturated lactones and with cyclic vinyl ethers. Part I

Résumé

The 1,3-dipolar cycloaddition of cyclic nitrones with electron-poor and electron-rich cyclic dipolarophiles (α,β-unsaturated lactones and vinyl ethers) is studied. The energies of the cycloaddition reactions have been investigated through molecular orbital calculations at the B3LYP/6-31+G(d) level theory. Different reaction channels and reactants approaches, effective in regio- and stereochemical preferences are discussed. The results were compared with experimental data to find a good agreement.

Domaines

Chimie

Dates et versions

hal-00352500 , version 1 (13-01-2009)

Identifiants

Citer

Sebastian Stecko, Konrad Pasniczek, Carine Michel, Anne Milet, Serge Perez, et al.. A DFT study of 1,3-dipolar cycloaddition reactions of 5-membered cyclic nitrones with α,β-unsaturated lactones and with cyclic vinyl ethers. Part I. Tetrahedron: Asymmetry, 2008, 19 (14), pp.1660-1669. ⟨10.1016/j.tetasy.2008.07.008⟩. ⟨hal-00352500⟩
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