Influence of ground-state conformations on the intramolecular amidofuran Diels-Alder reaction.
[reaction: see text] 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.
Bur
Scott K
SK
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Lynch
Stephen M
SM
Padwa
Albert
A
D000577:Amides / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation
D000577:Amides; D005663:Furans