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.
Synthesis and reactivity of a stable precursor of 2-cyano-1,3-butadiene
BARALDI, Pier Giovanni;BARCO, Achille;BENETTI, Simonetta;MANFREDINI, Stefano;POLLINI, Gian Piero;SIMONI, Daniele;ZANIRATO, Vinicio
1988
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.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
