π-strain-induced electrophilicity in small cycloalkynes: A DFT analysis of the polar cycloaddition of cyclopentyne towards enol ethers

Luis R. Domingo, Patricia Pérez, Renato Contreras

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

Small cycloalkynes possess a π-strain-induced electrophilicity related to the bending of the Csp3-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.

Original languageEnglish
Pages (from-to)498-506
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number2
DOIs
Publication statusPublished - 16 Jan 2006

Keywords

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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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