Tetrahedron p. 6451 - 6454 (1988)
Update date:2022-08-04
Topics:
Baraldi, Pier Giovanni
Barco, Achille
Benetti, Simonetta
Manfredini, Stefano
Pollini, Gian Piero
et.al.
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 (13)C NMR shows that in some cases the products are a mixture of regioisomeric cycloadducts.
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