Synthesis and catalytic activity of ruthenium complexes modified with chiral racemic per- and polyfluorooxaalkanoates

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F16%3A43902741" target="_blank" >RIV/60461373:22310/16:43902741 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/16:00467331
Result on the web
<a href="https://www.journals.elsevier.com/journal-of-fluorine-chemistry/" target="_blank" >https://www.journals.elsevier.com/journal-of-fluorine-chemistry/</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.jfluchem.2016.09.005" target="_blank" >10.1016/j.jfluchem.2016.09.005</a>

Result language
angličtina
Original language name
Synthesis and catalytic activity of ruthenium complexes modified with chiral racemic per- and polyfluorooxaalkanoates
Original language description
Silver salts of racemic 2H-perfluoro(3-oxahexanoic) (3a), perfluoro(2-methyl-3-oxahexanoic) (3b) and 2,3,3,3-tetrafluoro-2-methoxypropanoic acid (3c) gave with Hoveyda-Grubbs 2nd generation catalyst 4 or its bis(polyfiuoroalkylated) analogue 5 the corresponding bis(polyfluoroacylated) ruthenium complexes 1a-1c or 2a, 2b as mixtures of three diastereoisomers. Their catalytic activity in model ring-closing metathesis (RCM) reactions decreased in the order 1b-2b > 1a-2a > 1c due to increased steric hindrance around the catalytic centre in complexes 1a, 1c and 2a, as well as due to lower acidity of acid 3c resulting in lower electrophilicity of the complex 1c. Thus, the complexes 1b and 2b displayed high activity in RCM of bis-unsaturated malonates forming disubstituted (RCM2) or trisubstituted (RCM3) double bond and were even significantly active in the formation of tetrasubstituted bond (RCM4), while complexes 1a, 1c were active in RCM2 but inactive in RCM3. Moreover, the yield of RCM2 catalyzed with complex is was rather low.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
<a href="/en/project/GAP207%2F10%2F1533" target="_blank" >GAP207/10/1533: Fluorous carbenes, complexes and ionic liquids based on perfluoropolyether-substituted imidazolium salts and their applications</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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