Influence of Ground-State Conformations on the Intramolecular Amidofuran Diels−Alder Reaction

Various factors that influence the rate of the intramolecular Diels−Alder reaction of amidofurans were investigated with density functional theory calculations using the Becke3LYP/6-31G* model. Conformational effects imposed by the placement of a carbonyl group within the tether, combined with a rot...

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Bibliographic Details
Published in:Organic letters 2002-02, Vol.4 (4), p.473-476
Main Authors: Bur, Scott K, Lynch, Stephen M, Padwa, Albert
Format: Article
Language:English
Subjects:
Amides - chemistry
Chemical Phenomena
Chemistry, Physical
Cyclization
Furans - chemistry
Models, Molecular
Molecular Conformation
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Summary:Various factors that influence the rate of the intramolecular Diels−Alder reaction of amidofurans were investigated with density functional theory calculations using the Becke3LYP/6-31G* model. Conformational effects imposed by the placement of a carbonyl group within the tether, combined with a rotational bias about the C(2)−N bond, account for the observed rate differences in the thermal chemistry of these amidofurans.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016804g