Bj. Mcnelis et al., SYNTHETIC AND KINETIC-STUDIES OF SUBSTITUENT EFFECTS IN THE FURAN INTRAMOLECULAR DIELS-ALDER REACTION, Tetrahedron, 50(23), 1994, pp. 6767-6782
The Intramolecular Diels-Alder reactions (IMDA) of a series of 2-sulfo
ne 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 ra
te and 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 (CO(2)Me) in these system
s have been shown to be very reactive, cyclizing at ambient temperatur
e.