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Development of PhSCF2CF2SiMe3 as a Tandem Anion and Radical Tetrafluoroethylene Equivalent: Preparation of Tetrafluoroethyl-Substituted Alcohols and Tetrafluorotetrahydropyrans

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    0361473 - ÚOCHB 2012 RIV DE eng J - Journal Article
    Chernykh, Yana - Hlat-Glembová, Katarina - Klepetářová, Blanka - Beier, Petr
    Development of PhSCF2CF2SiMe3 as a Tandem Anion and Radical Tetrafluoroethylene Equivalent: Preparation of Tetrafluoroethyl-Substituted Alcohols and Tetrafluorotetrahydropyrans.
    European Journal of Organic Chemistry. -, č. 24 (2011), s. 4528-4531. ISSN 1434-193X. E-ISSN 1099-0690
    R&D Projects: GA ČR GAP207/11/0421
    Institutional research plan: CEZ:AV0Z40550506
    Keywords : fluorine * alkylation * nucleophilic addition * radical reactions * oxygen heterocycles
    Subject RIV: CC - Organic Chemistry
    Impact factor: 3.329, year: 2011

    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.
    Permanent Link: http://hdl.handle.net/11104/0198779

     
     
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