A. Padwa, M. Ishida, Cheryl L. Muller
Feb 1, 1992
Citations
0
Influential Citations
33
Citations
Journal
Journal of Organic Chemistry
Abstract
2,3-Dihalo-1-(phenysulfonyl)-1-propenes (DBP and DIP) are conveniently prepared by treating 1-(phenylsulfonyl)-1,2-propadiene with the appropriate halogen. These novel reagents undergo reaction with a variety of simple β-dicarbonyl anions to give substituted and annulated furans. When the reaction is carried out in polar solvents, 2,3,4-trisubstituted furans are formed. The reaction proceeds by an initial addition-elimination of the carbanion onto the vinyl carbon of the unsaturated sulfone which is followed by intramolecular ring closure on the enolate oxygen atom