Journal of Fluorine Chemistry p. 143 - 151 (1998)
Update date:2022-08-24
Topics:
Dmowski, Wojciech
Manko, Vladimir A.
Nowak, Ireneusz
Simple, three step synthesis of a new fluorine containing diene, 3-chloro-4-fluorothiophene-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.
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