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)]
Title
The Change of Aromaticity along a Diels-Alder Reaction Path
Published in
Organic Letters
Volume
5
Issue
7
Pages
1127-1130
Date
2003
ISSN
1523-7060
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)
