P. Baraldi, A. Barco, S. Benetti
1988
Citations
0
Influential Citations
19
Citations
Journal
Tetrahedron
Abstract
Abstract A new, productive synthesis of 3-cyano-2,5-dihydrothiophene-1,1-dioxide (3) is described. This substituted sulfolene serves as a stable precursor of 2-cyano-1,3-butadiene and can be used in the Diels-Alder reactions without isolation of the unstable diene. The Diels-Alder reactions of 2-cyano-1,3-butadiene appear to proceed in high yield only with electron-deficient dienophiles, but 13C NMR shows that in some cases the products are a mixture of regioisomeric cycloadducts.