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 bet...

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Bibliographic Details
Published inOrganic letters Vol. 8; no. 24; pp. 5573 - 5575
Main Authors Dolbier, William R, Mitani, Akira, Xu, Wei, Ghiviriga, Ion
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 23.11.2006
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Cyclization
Free Radicals - chemistry
Furans - chemical synthesis
Heterocyclic Compounds - chemical synthesis
Indicators and Reagents
Physical Sciences
Science & Technology
MEDICINAL CHEMISTRY
FURANS
FLUORINE
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0622662