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research article

The Change of Aromaticity along a Diels-Alder Reaction Path

Corminboeuf, Clemence  
•
Heine, Thomas
•
Weber, Jacques
2003
Organic Letters

Quinodimethanes are highly reactive toward dienophiles since Diels-Alder cycloaddn. results in an arom. product. D. functional-based 13C, 1H NMR, NICS, and MO-NICS calcns. indicate that the increase of arom. character of the developing benzenoid ring along the reaction path is esp. pronounced after the transition state is reached, even though the no. of pi orbitals decreases. The forming aliph. ring exhibits large ring current effects during the reaction. [on SciFinder (R)]

  • Details
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Type
research article
DOI
10.1021/ol034203e
Author(s)
Corminboeuf, Clemence  
Heine, Thomas
Weber, Jacques
Date Issued

2003

Published in
Organic Letters
Volume

5

Issue

7

Start page

1127

End page

1130

Subjects

Diels-Alder reaction enthalpy (assocd. with aromatization; the change of aromaticity along a Diels-Alder reaction path for quinodimethane dienophiles); NMR (chem. shift

•

13C

•

1H

•

and NICS; the change of aromaticity along a Diels-Alder reaction path for quinodimethane dienophiles); Potential barrier; Potential energy surface; Transition state structure (for Diels-Alder reaction; the change of aromaticity along a Diels-Alder reaction path for quinodimethane dienophiles); Antiaromaticity (of spectator ring in reactant; the change of aromaticity along a Diels-Alder reaction path for quinodimethane dienophiles); Aromaticity; Diels-Alder reaction; Dienophiles (the change of aromaticity along a Diels-Alder reaction path for quinodimethane dienophiles); Quinonoid compounds Role: CPS (Chemical process)

•

PEP (Physical

•

engineering or chemical process)

•

PRP (Properties)

•

RCT (Reactant)

•

PROC (Process)

•

RACT (Reactant or reagent) (the change of aromaticity along a Diels-Alder reaction path for quinodimethane dienophiles); Molecular orbital (pi

•

pi-aromaticity; the change of aromaticity along a Diels-Alder reaction path for quinodimethane dienophiles)

•

Diels Alder quinodimethane aromaticity

Note

CAN 138:337582

22-5

Physical Organic Chemistry

Department of Physical Chemistry,University of Geneva,Geneva,Switz.

Journal

written in English.

74-85-1 (Ethylene); 32796-95-5 (o-Quinodimethane) Role: CPS (Chemical process), PEP (Physical, engineering or chemical process), PRP (Properties), RCT (Reactant), PROC (Process), RACT (Reactant or reagent) (the change of aromaticity along a Diels-Alder reaction path for quinodimethane dienophiles); 119-64-2 (1,2,3,4-Tetrahydronaphthalene) Role: FMU (Formation, unclassified), PRP (Properties), FORM (Formation, nonpreparative) (the change of aromaticity along a Diels-Alder reaction path for quinodimethane dienophiles)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LCMD  
Available on Infoscience
October 22, 2007
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/13172
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