Synthesis of novel pentafluorosulfanylfurans. Two retro-Diels-Alder approaches.

Org Lett

Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA.

Published: November 2006

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].

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http://dx.doi.org/10.1021/ol0622662DOI Listing

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