Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 24, Pages 4528-4531Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100667
Keywords
Fluorine; Alkylation; Nucleophilic addition; Radical reactions; Oxygen heterocycles
Categories
Funding
- Academy of Sciences of the Czech Republic [AVZ40550506]
- Grant Agency of the Czech Republic [207/11/0421]
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PhSCF2CF2SiMe3 (1) was developed as a tandem anion and radical tetrafluoroethylene equivalent for the introduction of a CF2CF2 moiety. Fluoride-initiated nucleophilic additions of 1 to carbonyl compounds provide the corresponding alcohol adducts 2. Reduction of 2 gives tetafluoroethyl-containing alcohols 3, whereas 6-exo radical cyclizations of allyl ethers 4 yield tetrafluorotetrahydropyrans 5.
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