Phase-transfer catalysis in oxidations based on covalent bonding of hydrogen peroxide to amphiphilic flavinium salts
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F14%3A43898147" target="_blank" >RIV/60461373:22310/14:43898147 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/cctc.201402533" target="_blank" >http://dx.doi.org/10.1002/cctc.201402533</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/cctc.201402533" target="_blank" >10.1002/cctc.201402533</a>
Alternative languages
Result language
angličtina
Original language name
Phase-transfer catalysis in oxidations based on covalent bonding of hydrogen peroxide to amphiphilic flavinium salts
Original language description
The amphiphilic flavin derivatives 1,10-ethylene bridged 3-alkylalloxazinium salts (alkyl = butyl, octyl, dodecyl and hexadecyl) were shown to catalyse chemoselective oxidation of sulfides to sulfoxides with hydrogen peroxide in chloroform/water or dichloromethane/water systems. Efficiency of catalytic oxidation substantially depended on pH of the aqueous phase, reaching maximum values at pH 7. Under such conditions, complete conversion of aliphatic and aromatic sulfides occurred within a maximum of 24h while the non-catalysed reaction gave only traces of products. This new concept of two-phase oxidation utilises the activation and the increase in lipophilicity of hydrogen peroxide by its covalent bonding to the alloxazinium catalyst. Practical application in the synthesis of modafinil was demonstrated.
Czech name
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Czech description
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Classification
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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Result continuities
Project
<a href="/en/project/GAP207%2F12%2F0447" target="_blank" >GAP207/12/0447: Organocatalytic stereoselective oxidations using heterocyclic hydroperoxides</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2014
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ChemCatChem
ISSN
1867-3880
e-ISSN
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Volume of the periodical
6
Issue of the periodical within the volume
10
Country of publishing house
DE - GERMANY
Number of pages
4
Pages from-to
2843-2846
UT code for WoS article
000342795000015
EID of the result in the Scopus database
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