Literature DB >> 11041829

Do secondary orbital interactions really exist?

J I García1, J A Mayoral, L Salvatella.   

Abstract

A revision of the most typical examples used to illustrate the existence of secondary orbital interactions (SOI) has been achieved. However, our analysis indicates that no conclusive evidence can be obtained from these cases. All five examples proposed by Woodward and Hoffmann in The Conservation of Orbital Symmetry have been revisited. A combination of well-known mechanisms (such as solvent effects, steric interactions, hydrogen bonds, electrostatic forces, and others) can be invoked instead to justify the endo/exo selectivity of Diels-Alder reactions.

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Year:  2000        PMID: 11041829     DOI: 10.1021/ar0000152

Source DB:  PubMed          Journal:  Acc Chem Res        ISSN: 0001-4842            Impact factor:   22.384


  6 in total

1.  Chiral cyclopropenyl ketones: reactive and selective Diels-Alder dienophiles.

Authors:  Laural A Fisher; Natalee J Smith; Joseph M Fox
Journal:  J Org Chem       Date:  2013-03-11       Impact factor: 4.354

2.  Intramolecular Diels-Alder reactions of cycloalkenones: stereoselectivity, Lewis acid acceleration, and halogen substituent effects.

Authors:  Hung V Pham; Robert S Paton; Audrey G Ross; Samuel J Danishefsky; K N Houk
Journal:  J Am Chem Soc       Date:  2014-02-04       Impact factor: 15.419

3.  Highly selective Diels-Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole.

Authors:  Carlos H Escalante; Eder I Martínez-Mora; Carlos Espinoza-Hicks; Alejandro A Camacho-Dávila; Fernando R Ramos-Morales; Francisco Delgado; Joaquín Tamariz
Journal:  Beilstein J Org Chem       Date:  2020-06-17       Impact factor: 2.883

4.  Effect of an α-Methyl Substituent on the Dienophile on Diels-Alder endo:exo Selectivity.

Authors:  Olatz Larrañaga; Abel de Cózar
Journal:  ChemistryOpen       Date:  2019-01-15       Impact factor: 2.911

5.  The origin of the regiospecificity of acrolein dimerization.

Authors:  Ramiro F Quijano-Quiñones; Jareth Guadarrama-Moreno; Mariana Quesadas-Rojas; Gonzalo J Mena-Rejón; Carolina S Castro-Segura; David Cáceres-Castillo
Journal:  RSC Adv       Date:  2021-02-16       Impact factor: 3.361

6.  Molecular design principles towards exo-exclusive Diels-Alder reactions.

Authors:  Ci-Jhang Huang; Elise Y Li
Journal:  RSC Adv       Date:  2019-03-04       Impact factor: 3.361

  6 in total

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