The change of aromaticity along a Diels-Alder reaction path

Clémence Corminboeuf; Thomas Heine; Jacques Weber

doi:10.1021/ol034203e

The change of aromaticity along a Diels-Alder reaction path

Clémence Corminboeuf, Thomas Heine, Jacques Weber

Department of Chemistry

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

29 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 language	English
Pages (from-to)	1127-1130
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	7
DOIs	https://doi.org/10.1021/ol034203e
Publication status	Published - 2003 Apr 3

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol034203e

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AB - (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.

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The change of aromaticity along a Diels-Alder reaction path

Abstract

All Science Journal Classification (ASJC) codes

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