The change of aromaticity along a Diels-Alder reaction path

Clémence Corminboeuf, Thomas Heine, Jacques Weber

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

(Matrix presented) Quinodimethanes are highly reactive toward dienophiles since Diels-Alder cycloaddition results in an aromatic product. Density functional-based 13C, 1H NMR, NICS, and MO-NICS calculations indicate that the increase of aromatic character of the developing benzenoid ring along the reaction path is especially pronounced after the transition state is reached, even though the number of π orbitals decreases. The forming aliphatic ring exhibits large ring current effects during the reaction.

Original languageEnglish
Pages (from-to)1127-1130
Number of pages4
JournalOrganic Letters
Volume5
Issue number7
DOIs
Publication statusPublished - 2003 Apr 3

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'The change of aromaticity along a Diels-Alder reaction path'. Together they form a unique fingerprint.

Cite this