A DFT Analysis of the Strain-Induced Regioselective[2+2]Cycloaddition of Benzyne Possessing Fused Four-Membered Ring

L.   R.   Domingo; P.      Perez; R.      Contreras

doi:10.2174/1570178053399958

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 performed on the basis of the global and local electrophilicity of reagents correctly explain the observed reactivity and regioselectivity in this system.

Keywords: cycloadditions, benzyne, regioselectivity, angle strain, dft calculations

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Letters in Organic Chemistry

Title: A DFT Analysis of the Strain-Induced Regioselective[2+2]Cycloaddition of Benzyne Possessing Fused Four-Membered Ring

Volume: 2 Issue: 1

Author(s): L. R. Domingo, P. Perez and R. Contreras

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Keywords: cycloadditions, benzyne, regioselectivity, angle strain, dft calculations

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 performed on the basis of the global and local electrophilicity of reagents correctly explain the observed reactivity and regioselectivity in this system.

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Domingo R. L., Perez P. and Contreras R., A DFT Analysis of the Strain-Induced Regioselective[2+2]Cycloaddition of Benzyne Possessing Fused Four-Membered Ring, Letters in Organic Chemistry 2005; 2 (1) . https://dx.doi.org/10.2174/1570178053399958