Effect of electron-withdrawing substituents on the inverse-electron demand diels-alder reaction of 2-aminopyrroles and 1,3,5-triazines

Michael De Rosa, David Arnold, Eric Blythe, Martillas S. Farrell, Tamika Seals, Kristin Wills, Miroslav Medved

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Inverse-electron demand Diels-Alder reactions of 1,3,5-triazines and 2-aminopyrroles are facilitated by electron-withdrawing groups (EWG) on both reactants. Whereas HOMO-LUMO calculations predict that EWG on 2-aminopyrroles should lower the relative rate of reaction. This apparent contradiction can be explained if the reaction cascade is under equilibrium control with at least one reversible step.

Original languageEnglish (US)
Pages (from-to)97-100
Number of pages4
JournalHeterocyclic Communications
Volume13
Issue number2-3
DOIs
StatePublished - Jan 1 2007

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Triazines
Electrons

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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De Rosa, Michael ; Arnold, David ; Blythe, Eric ; Farrell, Martillas S. ; Seals, Tamika ; Wills, Kristin ; Medved, Miroslav. / Effect of electron-withdrawing substituents on the inverse-electron demand diels-alder reaction of 2-aminopyrroles and 1,3,5-triazines. In: Heterocyclic Communications. 2007 ; Vol. 13, No. 2-3. pp. 97-100.
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abstract = "Inverse-electron demand Diels-Alder reactions of 1,3,5-triazines and 2-aminopyrroles are facilitated by electron-withdrawing groups (EWG) on both reactants. Whereas HOMO-LUMO calculations predict that EWG on 2-aminopyrroles should lower the relative rate of reaction. This apparent contradiction can be explained if the reaction cascade is under equilibrium control with at least one reversible step.",
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Effect of electron-withdrawing substituents on the inverse-electron demand diels-alder reaction of 2-aminopyrroles and 1,3,5-triazines. / De Rosa, Michael; Arnold, David; Blythe, Eric; Farrell, Martillas S.; Seals, Tamika; Wills, Kristin; Medved, Miroslav.

In: Heterocyclic Communications, Vol. 13, No. 2-3, 01.01.2007, p. 97-100.

Research output: Contribution to journalArticle

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AU - Seals, Tamika

AU - Wills, Kristin

AU - Medved, Miroslav

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