Synthetic and Kinetic Studies of Substituent Effects in the Furan Intramolecular Diel-Alder Reaction

Article abstract of DOI:10.1016/S0040-4020(01)81331-4

The intramolecular Diels-Alder reactions (IMDA) of a series of 2-sulfone substituted 1-furyl-4-penten-1-ols, 5a-c, have been studied.As the steric demands of the alkyl group on the sulfone was increased the rate and the product yields in the IMDA reaction have also been observed to increase.The kinetics of these systems have been studied in detail as well as solvent effects to quantify substituent group effects in the cyclization reactions.Activated dienophiles (CO2Me) in these systems have been shown to be very reactive, cyclizing at ambient temperature.