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