Synthesis of novel pentafluorosulfanylfurans. Two retro-Diels-Alder approaches.
The first examples of furan substituted with an SF5 group are reported. 3-pentafluorosulfanylfurans were prepared from their respective 2-pentafluorosulfanyl-5-cyano-7-oxabicyclo[2.2.1]hept-2-ene precursors via retro-Diels-Alder reactions. Also, a tandem cycloaddition/retrocycloaddition reaction between 4-phenyloxazole and 1-pentafluorosulfanylhex-1-yne was used to prepare 3-pentafluorosulfanyl-4-butylfuran. [reaction: see text].
Dolbier
William R
WR
Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. wrd@chem.ufl.edu
Mitani
Akira
A
Xu
Wei
W
Ghiviriga
Ion
I
D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis; D007202:Indicators and Reagents
D005609:Free Radicals; D005663:Furans; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents