A selective and efficient method for alcohol oxidations mediated by N-oxoammonium salts in combination with sodium bromite

Inokuchi, Tsutomu; Matsumoto, Sigeaki; Nishiyama, Tokio; Torii, Sigeru

doi:10.1021/jo00289a016

Cited by 158 publications

(63 citation statements)

References 3 publications

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“…Amberlite·-NEt 3 + /ClO 2 À was successfully used as a polymeric secondary oxidant [43] for similar transformations, and good results were also achieved when NaBrO 2 was used as a secondary oxidant. [44] Another useful cooxidant that is frequently applied in TEMPO-mediated oxidations is bis(acetoxyiodo)benzene (BAIB, PhI(OAc) 2 ). [45] The mechanism for the regeneration of the oxammonium salt by PhI(OAc) 2 is not fully understood.…”

Section: Oxidation Of Alcoholsmentioning

confidence: 99%

Nitroxides: Applications in Synthesis and in Polymer Chemistry

2011

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This Review describes the application of nitroxides to synthesis and polymer chemistry. The synthesis and physical properties of nitroxides are discussed first. The largest section focuses on their application as stoichiometric and catalytic oxidants in organic synthesis. The oxidation of alcohols and carbanions, as well as oxidative C-C bond-forming reactions are presented along with other typical oxidative transformations. A section is also dedicated to the extensive use of nitroxides as trapping reagents for C-centered radicals in radical chemistry. Alkoxyamines derived from nitroxides are shown to be highly useful precursors of C-centered radicals in synthesis and also in polymer chemistry. The last section discusses the basics of nitroxide-mediated radical polymerization (NMP) and also highlights new developments in the synthesis of complex polymer architectures.

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Section: Oxidation Of Alcoholsmentioning

confidence: 99%

Nitroxides: Applications in Synthesis and in Polymer Chemistry

2011

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“…Amberit·NEt 3 /ClO 2 À wurde erfolgreich als polymeres Cooxidans für ähnliche Umsetzungen verwendet, [43] ebenso wurden mit NaBrO 2 als Sekundäroxidans gute Ergebnisse erzielt. [44] Ein weiteres Cooxidationsmittel, das häufig in TEMPOvermittelten Oxidationen verwendet wird, ist Bisacetoxyiodbenzol (PhI(OAc) 2 , BAIB). [45] Der Mechanismus der Regenerierung des Oxoammoniumsalzes mit PhI(OAc) 2 Ausbeute selektiv zum Aldehyd 16 oxidiert.…”

Section: Synthese Von Nitroxidenunclassified

Nitroxide: Anwendungen in der Synthese und in der Polymerchemie

2011

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Nitroxide werden in der Synthese und in der Polymerchemie verwendet. In diesem Aufsatz werden zunächst Methoden zur Herstellung von Nitroxiden und deren physikalische Eigenschaften besprochen. Der folgende Abschnitt beschreibt die Verwendung von Nitroxiden als stöchiometrische und katalytische Oxidationsmittel in der organischen Synthese. Die Oxidation von Alkoholen und Carbanionen spielt dabei ebenso eine wichtige Rolle wie oxidative C‐C‐Bindungsknüpfungen. Anschließend widmet sich ein Abschnitt der Rolle von Nitroxiden als Abfangreagentien für C‐zentrierte Radikale in der Radikalchemie. Nitroxide, die sich von Alkoxyaminen ableiten, fungieren als nützliche Ausgangsmaterialien für C‐zentrierte Radikale, deren Einsatz in der Synthese und in der Polymerchemie beschrieben wird. Der letzte Abschnitt stellt die Grundlagen der Nitroxid‐vermittelten Polymerisation (NMP) vor und zeigt neuere Entwicklungen beim Design komplexer Polymerarchitekturen auf.

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“…A oxidação de álcoois utilizando o TEMPO em quantidades catalíticas tem sido realizada empregando diferentes re-oxidantes, dentre os quais podem-se destacar: o ácido meta-cloroperbenzóico (m-AMCPB) 25 , hipoclorito de sódio (NaClO) 26 , clorito de sódio (NaClO 2 ) 27 , hipoclorito de ter-butila (ClOt-Bu) 28 , bromito de sódio (NaBrO) 29 32 , peróxido em presença de prata 33 , oxigênio em combinação com sais de elevada valência 34 e eletrooxidação 35 . O desenvolvimento de reações de oxidação de álcoois, utilizando radicais nitroxilas em quantidades catalíticas foi descrita pela primeira vez por Cella e colaboradores que, empregando o cloridrato de 2,2,6,6-tetrametilpiperidina (TMP.HCl) e o ácido metacloroperbenzóico (m-AMCPB) 25 , obtiveram uma inesperada reação de oxidação de álcoois.…”

Section: Metodologias De Oxidação De áLcoois Utilizando O Tempo Em Quunclassified

Utilização do TEMPO (N-oxil-2,2,6,6-tetrametilpiperidina) na oxidação de álcoois primários e secundários

Souza¹

2004

Quím. Nova

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A selective and efficient method for alcohol oxidations mediated by N-oxoammonium salts in combination with sodium bromite

Cited by 158 publications

References 3 publications

Nitroxides: Applications in Synthesis and in Polymer Chemistry

Nitroxides: Applications in Synthesis and in Polymer Chemistry

Nitroxide: Anwendungen in der Synthese und in der Polymerchemie

Utilização do TEMPO (N-oxil-2,2,6,6-tetrametilpiperidina) na oxidação de álcoois primários e secundários

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