High-level computational study of the site-, facial- and stereoselectivities for the Diels-Alder reaction between o-benzoquinone and norbornadiene

Davor Margetic, Martin R. Johnston, Ronald N. Warrener

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Ab initio and DFT quantum chemical calculations have been applied to a study of the Diels-Alder reaction of o-benzoquinone as diene and norbornadiene as dienophile. Transition states for the different reactions are located and activation energies estimated. The prefered exo-π-facial selectivity and exo,endo-stereoselectivity exhibited in this cycloaddition are readily predicted using RHF/3-21G or higher levels of calculations. Differences between experimentally observed results and calculations may be explained by the postulation of a second, nonconcerted biradical mechanism leading to formation of hetero Diels-Alder products.

Original languageEnglish
Pages (from-to)1417-1428
Number of pages12
JournalMolecules
Volume5
Issue number12
Publication statusPublished - 22 Dec 2000
Externally publishedYes

Bibliographical note

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Keywords

  • Ab initio and DFT calculations
  • Cycloaddition
  • Inverse electron-demand
  • O-benzoquinones

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