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Catalytic Oxidation of Partially and Fully Fluorinated Olefins with Osmium Tetroxide
Author(s) -
Herrmann Wolfgang A.,
Eder Stefan J.,
Scherer Wolfgang
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199213451
Subject(s) - osmium tetroxide , hydroxylation , chemistry , catalysis , organic chemistry , hydrolysis , olefin fiber , osmium , ozonolysis , ruthenium , electron microscope , physics , optics , enzyme
A commonly held conception must be revised. The OsO 4 ‐catalyzed cis ‐hydroxylation of olefins was never tested with fluorinated olefins, because it was assumed that electron‐poor olefins would not react with OsO 4 . But under the standard reaction conditions even perfluorinated olefins can be converted into osmate esters such as 1 quickly and quantitatively. Their subsequent hydrolysis provides cis ‐diols, ketones, or 1,2‐diketones.