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

doi:10.1515/HC.2007.13.2-3.97

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

Penn State Brandywine

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

11 Scopus citations

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 language	English (US)
Pages (from-to)	97-100
Number of pages	4
Journal	Heterocyclic Communications
Volume	13
Issue number	2-3
DOIs	https://doi.org/10.1515/HC.2007.13.2-3.97
State	Published - 2007

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1515/HC.2007.13.2-3.97

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

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.",

author = "\{De Rosa\}, Michael and David Arnold and Eric Blythe and Farrell, \{Martillas S.\} and Tamika Seals and Kristin Wills and Miroslav Medved",

note = "Funding Information: This work was supported by a grant (CHE-0110801) from the National Science Foundation. We thank Dr. J. Honovich (Drexel University) for mass spectra and Prof. J. K. Snyder (Boston University) for pre-prints and a 1,3,5-triazine sample.",

year = "2007",

doi = "10.1515/HC.2007.13.2-3.97",

language = "English (US)",

volume = "13",

pages = "97--100",

journal = "Heterocyclic Communications",

issn = "0793-0283",

publisher = "Walter de Gruyter GmbH",

number = "2-3",

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TY - JOUR

T1 - Effect of electron-withdrawing substituents on the inverse-electron demand diels-alder reaction of 2-aminopyrroles and 1,3,5-triazines

AU - De Rosa, Michael

AU - Arnold, David

AU - Blythe, Eric

AU - Farrell, Martillas S.

AU - Seals, Tamika

AU - Wills, Kristin

AU - Medved, Miroslav

N1 - Funding Information: This work was supported by a grant (CHE-0110801) from the National Science Foundation. We thank Dr. J. Honovich (Drexel University) for mass spectra and Prof. J. K. Snyder (Boston University) for pre-prints and a 1,3,5-triazine sample.

PY - 2007

Y1 - 2007

N2 - 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.

AB - 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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U2 - 10.1515/HC.2007.13.2-3.97

DO - 10.1515/HC.2007.13.2-3.97

M3 - Article

AN - SCOPUS:34547640074

SN - 0793-0283

VL - 13

SP - 97

EP - 100

JO - Heterocyclic Communications

JF - Heterocyclic Communications

IS - 2-3

ER -

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

Abstract

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