A criterion to demarcate the dual Diels-Alder and σ-complex behaviour of aromatic and heteroaromatic superelectrophiles

R. Goumont; F. Terrier; D. Vichard; S. Lakhdar; Julian M. Dust; E. Buncel

doi:10.1016/j.tetlet.2005.09.159

A criterion to demarcate the dual Diels-Alder and σ-complex behaviour of aromatic and heteroaromatic superelectrophiles

R. Goumont
, F. Terrier
, D. Vichard
, S. Lakhdar
, Julian M. Dust
, E. Buncel

Université Versailles-Saint Quentin
Department of Chemistry
Memorial University of New Foundland
Department of Chemistry
Queen's University

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

22 Citations (Scopus)

Abstract

A frontier demarcating superelectrophilic compounds that undergo both Diels-Alder reactivity and σ-complexation reactions, from traditional electrophiles, is afforded through the thermodynamic tendency for σ-complexation as defined by the pK_a values for H₂O addition to electron-deficient aromatic and heteroaromatic substrates.

Original language	English
Pages (from-to)	8363-8367
Number of pages	5
Journal	Tetrahedron Letters
Volume	46
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2005.09.159
Publication status	Published - 28 Nov 2005
Externally published	Yes

Keywords

Diels-Alder cycloadditions
Heterocycles
Nitrobenzofuroxan
Superelectrophiles
σ-Complexation

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10.1016/j.tetlet.2005.09.159

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abstract = "A frontier demarcating superelectrophilic compounds that undergo both Diels-Alder reactivity and σ-complexation reactions, from traditional electrophiles, is afforded through the thermodynamic tendency for σ-complexation as defined by the pKa values for H2O addition to electron-deficient aromatic and heteroaromatic substrates.",

keywords = "Diels-Alder cycloadditions, Heterocycles, Nitrobenzofuroxan, Superelectrophiles, σ-Complexation",

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T1 - A criterion to demarcate the dual Diels-Alder and σ-complex behaviour of aromatic and heteroaromatic superelectrophiles

AU - Goumont, R.

AU - Terrier, F.

AU - Vichard, D.

AU - Lakhdar, S.

AU - Dust, Julian M.

AU - Buncel, E.

PY - 2005/11/28

Y1 - 2005/11/28

N2 - A frontier demarcating superelectrophilic compounds that undergo both Diels-Alder reactivity and σ-complexation reactions, from traditional electrophiles, is afforded through the thermodynamic tendency for σ-complexation as defined by the pKa values for H2O addition to electron-deficient aromatic and heteroaromatic substrates.

AB - A frontier demarcating superelectrophilic compounds that undergo both Diels-Alder reactivity and σ-complexation reactions, from traditional electrophiles, is afforded through the thermodynamic tendency for σ-complexation as defined by the pKa values for H2O addition to electron-deficient aromatic and heteroaromatic substrates.

KW - Diels-Alder cycloadditions

KW - Heterocycles

KW - Nitrobenzofuroxan

KW - Superelectrophiles

KW - σ-Complexation

UR - https://www.scopus.com/pages/publications/27644455025

U2 - 10.1016/j.tetlet.2005.09.159

DO - 10.1016/j.tetlet.2005.09.159

M3 - Article

AN - SCOPUS:27644455025

SN - 0040-4039

VL - 46

SP - 8363

EP - 8367

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

A criterion to demarcate the dual Diels-Alder and σ-complex behaviour of aromatic and heteroaromatic superelectrophiles

Abstract

Keywords

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