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.