Title of article :
A DFT Analysis of the Strain-Induced Regioselective[2+2]Cycloaddition of Benzyne Possessing Fused Four-Membered Ring
Author/Authors :
Domingo, L.R. Universidad de Valencia - Instituto de Ciencia Molecular - Departamento de Química Orgánica, Spain , Pérez, P. Universidad Andrés Bello - Facultad de Ecología y Recursos Naturales - Departamento de Ciencias Químicas, Chile , Contreras, R. Universidad de Chile - Facultad de Ciencias - Departamento de Química, Chile
Abstract :
The regioselective [2+2] cycloaddition of a substituted benzyne possessing a fused four-membered ring to a ketene acetal has been theoretically studied. This cycloaddition presents a two-step mechanism that is initiated by the nucleophilic attack to the benzyne to give a zwitterionic intermediate. The analysis performedon the basis of the global and local electrophilicity of reagents correctly explain the observed reactivity and regioselectivity in this system.
Keywords :
[2+2] Cycloadditions , benzyne , regioselectivity , angle strain , DFT calculations
Journal title :
letters in organic chemistry
Journal title :
letters in organic chemistry
