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

doi:10.1002/ejoc.200500466

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

Exact Sciences School

Research output: Contribution to journal › Article › peer-review

29 Citations (Scopus)

Abstract

Small cycloalkynes possess a π-strain-induced electrophilicity related to the bending of the C^sp3-C^sp-C^sp 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 language	English
Pages (from-to)	498-506
Number of pages	9
Journal	European Journal of Organic Chemistry
Issue number	2
DOIs	https://doi.org/10.1002/ejoc.200500466
Publication status	Published - 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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10.1002/ejoc.200500466

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AU - Contreras, Renato

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AB - 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.

KW - Cycloadditions

KW - Cycloalkynes

KW - Density functional calculations

KW - Electrophilicity

KW - Strain

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

Abstract

Keywords

ASJC Scopus subject areas

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