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Development of PhSCF 2 CF 2 SiMe 3 as a Tandem Anion and Radical Tetrafluoroethylene Equivalent: Preparation of Tetrafluoroethyl‐Substituted Alcohols and Tetrafluorotetrahydropyrans
Author(s) -
Chernykh Yana,
HlatGlembová Katarina,
Klepetářová Blanka,
Beier Petr
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100667
Subject(s) - tetrafluoroethylene , chemistry , moiety , tandem , fluoride , adduct , yield (engineering) , medicinal chemistry , nucleophile , alcohol , organic chemistry , inorganic chemistry , catalysis , materials science , copolymer , composite material , metallurgy , polymer
PhSCF 2 CF 2 SiMe 3 ( 1 ) was developed as a tandem anion and radical tetrafluoroethylene equivalent for the introduction of a CF 2 CF 2 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 .