W. Dmowski, Vladimir A. Manko, I. Nowak
Mar 27, 1998
Citations
0
Influential Citations
17
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract Simple, three step synthesis of a new fluorine containing diene, 3-chloro-4-fiuorothiophene-1,1-dioxide (4) , from commercially available 3-sulpholene (1) has been developed. The synthetic value of compound 4 as a Diels-Alder diene has been demonstrated by its reactions with various type of dienophiles: acetylenes, alkenes, furans, quinone and anthracene. The reactions proceed with high regioselectivity to give good yields of 3-fluoro-4-chloro substituted aromatics or cyclic chlorofluorodienes. In reactions with alkenes, immediate aromatisation often occurs. In some instances, when reacted with a diene, compound 4 behaves as a dienophile.