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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

  • Czech description

Classification

  • Type

    J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

  • CEP classification

    CC - Organic chemistry

  • OECD FORD branch

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

  • 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