About: Insight into the catalytic activity of alloxazinium and isoalloxazinium salts in the oxidations of sulfides and amines with hydrogen peroxide

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About: Insight into the catalytic activity of alloxazinium and isoalloxazinium salts in the oxidations of sulfides and amines with hydrogen peroxide Goto Sponge NotDistinct Permalink

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Description	In addition to the already known organocatalysts dihydro-5-ethylalloxazines 1-H2 and 5-ethylisoalloxazinium salts 2, other derivatives of alloxazines and isoalloxazines (flavins) have been shown to catalyze the oxidation of sulfides to sulfoxides with hydrogen peroxide with high efficiency. In the alloxazine series, the C4a-methoxy adduct 1-OCH3 or 5-ethylalloxazinium salts 1 can also be used, but the latter only in the presence of a base, as a co-catalyst. In the isoalloxazine series, the C4a-hydroxy adduct 2-OH or dihydroform 2-H2 can also be utilized but only in the presence of the catalytic amount of an acid. On the other hand, only alloxazine derivatives, i.e. dihydroalloxazines 1-H2 and their methoxy adducts 1-OCH3 or alloxazinium salts 1 can be used as catalysts for the oxidation of tertiary amines, as the catalytic activity of isoalloxazinium salts 1 and their derivatives is inhibited under basic conditions. The different reactivity of the alloxazinium and isoalloxazinium catalysts is a consequence of the change of the rate determining step in the catalytic cycle, resulting from their significantly different ability to react with nucleophiles. In addition to the already known organocatalysts dihydro-5-ethylalloxazines 1-H2 and 5-ethylisoalloxazinium salts 2, other derivatives of alloxazines and isoalloxazines (flavins) have been shown to catalyze the oxidation of sulfides to sulfoxides with hydrogen peroxide with high efficiency. In the alloxazine series, the C4a-methoxy adduct 1-OCH3 or 5-ethylalloxazinium salts 1 can also be used, but the latter only in the presence of a base, as a co-catalyst. In the isoalloxazine series, the C4a-hydroxy adduct 2-OH or dihydroform 2-H2 can also be utilized but only in the presence of the catalytic amount of an acid. On the other hand, only alloxazine derivatives, i.e. dihydroalloxazines 1-H2 and their methoxy adducts 1-OCH3 or alloxazinium salts 1 can be used as catalysts for the oxidation of tertiary amines, as the catalytic activity of isoalloxazinium salts 1 and their derivatives is inhibited under basic conditions. The different reactivity of the alloxazinium and isoalloxazinium catalysts is a consequence of the change of the rate determining step in the catalytic cycle, resulting from their significantly different ability to react with nucleophiles. (en)
Title	Insight into the catalytic activity of alloxazinium and isoalloxazinium salts in the oxidations of sulfides and amines with hydrogen peroxide Insight into the catalytic activity of alloxazinium and isoalloxazinium salts in the oxidations of sulfides and amines with hydrogen peroxide (en)
skos:prefLabel	Insight into the catalytic activity of alloxazinium and isoalloxazinium salts in the oxidations of sulfides and amines with hydrogen peroxide Insight into the catalytic activity of alloxazinium and isoalloxazinium salts in the oxidations of sulfides and amines with hydrogen peroxide (en)
skos:notation	RIV/60461373:22310/12:43893696!RIV13-GA0-22310___
http://linked.open...avai/predkladatel	Fakulta chemické technologie
http://linked.open...avai/riv/aktivita	P
http://linked.open...avai/riv/aktivity	P(GAP207/12/0447)
http://linked.open...iv/cisloPeriodika	Neuveden
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Cibulka, Radek Ménová, Petra
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	142007
http://linked.open...ai/riv/idVysledku	RIV/60461373:22310/12:43893696
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Hydrogen peroxide; N-oxidation; Sulfoxidation; Flavinium salts; Organocatalysis (en)
http://linked.open.../riv/klicoveSlovo	Flavinium salts N-oxidation Hydrogen peroxide Organocatalysis Sulfoxidation
http://linked.open...odStatuVydavatele	BE - Belgické království
http://linked.open...ontrolniKodProRIV	[43CBAE96EA23]
http://linked.open...i/riv/nazevZdroje	Journal Of Molecular Catalysis A-Chemical
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	2 (xsd:int)
http://linked.open...cetTvurcuVysledku	2 (xsd:int)
http://linked.open...vavai/riv/projekt	Organocatalytic stereoselective oxidations using heterocyclic hydroperoxides
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	363
http://linked.open...iv/tvurceVysledku	Cibulka, Radek Ménová, Petra
http://linked.open...ain/vavai/riv/wos	000309443400047
issn	1381-1169
number of pages	9 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.molcata.2012.07.012
http://localhost/t...ganizacniJednotka	22310
is http://linked.open...avai/riv/vysledek of	Insight into the catalytic activity of alloxazinium and isoalloxazinium salts in the oxidations of sulfides and amines with hydrogen peroxide

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