A DFT analysis of the strain-induced regioselective[2+2]cycloaddition of benzyne possessing fused four-membered ring

L. R. Domingo, P. Pérez, R. Contreras

Research output: Contribution to journalReview articlepeer-review

14 Citations (Scopus)

Abstract

The regioselective [2+2] cycloaddition of a substituted benzyne possessing a fused four-membered ring to a ketene acetal has been theoretically studied. This cycloaddition presents a two-step mechanism that is initiated by the nucleophilic attack to the benzyne to give a zwitterionic intermediate. The analysis performed on the basis of the global and local electrophilicity of reagents correctly explain the observed reactivity and regioselectivity in this system.

Original languageEnglish
Pages (from-to)68-73
Number of pages6
JournalLetters in Organic Chemistry
Volume2
Issue number1
DOIs
Publication statusPublished - 1 Feb 2005

Keywords

  • [2+2] Cyloadditions
  • Angle strain
  • Benzyne
  • DFT calculations
  • Regioselectivity

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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