About: Phase-transfer catalysis in oxidations based on covalent bonding of hydrogen peroxide to amphiphilic flavinium salts

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About: Phase-transfer catalysis in oxidations based on covalent bonding of hydrogen peroxide to amphiphilic flavinium salts Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
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 24 h 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. 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 24 h 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. (en)
Title	Phase-transfer catalysis in oxidations based on covalent bonding of hydrogen peroxide to amphiphilic flavinium salts Phase-transfer catalysis in oxidations based on covalent bonding of hydrogen peroxide to amphiphilic flavinium salts (en)
skos:prefLabel	Phase-transfer catalysis in oxidations based on covalent bonding of hydrogen peroxide to amphiphilic flavinium salts Phase-transfer catalysis in oxidations based on covalent bonding of hydrogen peroxide to amphiphilic flavinium salts (en)
skos:notation	RIV/60461373:22310/14:43898147!RIV15-GA0-22310___
http://linked.open...avai/riv/aktivita	P
http://linked.open...avai/riv/aktivity	P(GAP207/12/0447)
http://linked.open...iv/cisloPeriodika	10
http://linked.open...vai/riv/dodaniDat	2015
http://linked.open...aciTvurceVysledku	Zelenka, Jan Hampl, František Klímová, Kateřina Cibulka, Radek Hartman, Tomáš
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Vysoká škola chemicko-technologická v Praze / Fakulta chemické technologie
http://linked.open...dnocenehoVysledku	36408
http://linked.open...ai/riv/idVysledku	RIV/60461373:22310/14:43898147
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	sulfoxides; organocatalysis; peroxides; oxidation; Phase-transfer catalysis (en)
http://linked.open.../riv/klicoveSlovo	Phase-transfer catalysis oxidation organocatalysis peroxides sulfoxides
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[D96496034AF9]
http://linked.open...i/riv/nazevZdroje	ChemCatChem
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	5 (xsd:int)
http://linked.open...cetTvurcuVysledku	5 (xsd:int)
http://linked.open...vavai/riv/projekt	Organocatalytic stereoselective oxidations using heterocyclic hydroperoxides
http://linked.open...UplatneniVysledku	2014
http://linked.open...v/svazekPeriodika	6
http://linked.open...iv/tvurceVysledku	Cibulka, Radek Zelenka, Jan Hampl, František Klímová, Kateřina Hartman, Tomáš
http://linked.open...ain/vavai/riv/wos	000342795000015
issn	1867-3880
number of pages	4 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/cctc.201402533
http://localhost/t...ganizacniJednotka	22310

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