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π-Strain-Induced Electrophilicity in Small Cycloalkynes: A DFT Analysis of the Polar Cycloaddition of Cyclopentyne towards Enol Ethers

  1. Luis R. Domingo1,
  2. Patricia Pérez2,3,
  3. Renato Contreras3

Article first published online: 31 OCT 2005

DOI: 10.1002/ejoc.200500466

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2006, Issue 2, pages 498–506, January 2006

Additional Information

How to Cite

Domingo, L. R., Pérez, P. and Contreras, R. (2006), π-Strain-Induced Electrophilicity in Small Cycloalkynes: A DFT Analysis of the Polar Cycloaddition of Cyclopentyne towards Enol Ethers. Eur. J. Org. Chem., 2006: 498–506. doi: 10.1002/ejoc.200500466

Author Information

  1. 1

    Instituto de Ciencia Molecular, Unidad de Investigación de Química Orgánica Teórica, Universidad de Valencia, Dr. Moliner 50, 46100 Burjassot, Valencia, Spain

  2. 2

    Departamento de Ciencias Químicas, Facultad de Ecología y Recursos Naturales, Universidad Andrés Bello, República 275, Santiago, Chile

  3. 3

    Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile

Publication History

  1. Issue published online: 2 JAN 2006
  2. Article first published online: 31 OCT 2005
  3. Manuscript Received: 24 JUN 2005

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Keywords:

  • Cycloadditions;
  • Cycloalkynes;
  • Density functional calculations;
  • Electrophilicity;
  • Strain

Abstract

Small cycloalkynes possess a π-strain-induced electrophilicity related to the bending of the Cmath image–Csp–Csp bond angle. For cyclopentyne and benzyne, the electrophilicity index defined in the context of density functional theory gives a coherent rationale for the reactivity of these cycloalkynes, which may act as electrophiles in polar cycloaddition reactions toward enol ethers. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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