Two-phase Oxidations with Aqueous Hydrogen Peroxide Catalysed by Amphiphilic Pyridinium and Diazinium Salts

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F15%3A43900599" target="_blank" >RIV/60461373:22310/15:43900599 - isvavai.cz</a>

Výsledek na webu

<a href="http://onlinelibrary.wiley.com/doi/10.1002/adsc.201500687/epdf" target="_blank" >http://onlinelibrary.wiley.com/doi/10.1002/adsc.201500687/epdf</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/adsc.201500687" target="_blank" >10.1002/adsc.201500687</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Two-phase Oxidations with Aqueous Hydrogen Peroxide Catalysed by Amphiphilic Pyridinium and Diazinium Salts

Popis výsledku v původním jazyce

Amphiphilic pyridinium and diazinium salts were shown to be effective catalysts in two-phase (water/chloroform or water/dichloromethane) sulfoxidations and N-oxidations with hydrogen peroxide under mild conditions. This unprecedented oxidation method utilizes covalent bonding of hydrogen peroxide to a simple pyridinium or diazinium nucleus to increase the lipophilicity of the hydroperoxide species and to subsequently activate it for oxidations in a non-polar medium. The catalytic efficiency was found todepend on the type of heteroarenium core and on the lipophilicity of the catalyst. Five series of heteroarenium catalysts were prepared and investigated: 1-Alkyl-3,5-dicyanopyridinium, 1-alkyl-3,5-dinitropyridinium, 1-alkyl-3-cyanopyrazinium, 1-alkyl-4-cyanopyrimidinium and 1-alkyl-4-(trifluoromethyl)pyrimidinium triflates (alkyl = butyl, hexyl, octyl, decyl, dodecyl and hexadecyl). Among them, the 1-octyl-3,5-dinitropyridinium and 1-decyl-4-(trifluoromethyl)pyrimidinium triflates were

Název v anglickém jazyce

Two-phase Oxidations with Aqueous Hydrogen Peroxide Catalysed by Amphiphilic Pyridinium and Diazinium Salts

Popis výsledku anglicky

Amphiphilic pyridinium and diazinium salts were shown to be effective catalysts in two-phase (water/chloroform or water/dichloromethane) sulfoxidations and N-oxidations with hydrogen peroxide under mild conditions. This unprecedented oxidation method utilizes covalent bonding of hydrogen peroxide to a simple pyridinium or diazinium nucleus to increase the lipophilicity of the hydroperoxide species and to subsequently activate it for oxidations in a non-polar medium. The catalytic efficiency was found todepend on the type of heteroarenium core and on the lipophilicity of the catalyst. Five series of heteroarenium catalysts were prepared and investigated: 1-Alkyl-3,5-dicyanopyridinium, 1-alkyl-3,5-dinitropyridinium, 1-alkyl-3-cyanopyrazinium, 1-alkyl-4-cyanopyrimidinium and 1-alkyl-4-(trifluoromethyl)pyrimidinium triflates (alkyl = butyl, hexyl, octyl, decyl, dodecyl and hexadecyl). Among them, the 1-octyl-3,5-dinitropyridinium and 1-decyl-4-(trifluoromethyl)pyrimidinium triflates were

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/GAP207%2F12%2F0447" target="_blank" >GAP207/12/0447: Organokatalytické stereoselektivní oxidace s využitím heterocyklických hydroperoxidů</a><br>

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2015

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

ADVANCED SYNTHESIS &amp; CATALYSIS

ISSN

1615-4150

e-ISSN

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Svazek periodika

357

Číslo periodika v rámci svazku

16-17

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

14

Strana od-do

3573-3586

Kód UT WoS článku

000368342400025

EID výsledku v databázi Scopus

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