Oxidative Rearrangement of Tertiary Allylic Alcohols Employing Oxoammonium Salts

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Abstract

Practical and highly efficient methods for oxidative rearrangement of tertiary allylic alcohols to β-substituted α,β-unsaturated carbonyl compounds employing oxoammonium salts are described. The methods developed are applicable to acyclic substrates as well as medium membered ring substrates and macrocyclic substrates. The counteranion of the oxoammonium salt plays crucial roles on this oxidative rearrangement.

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This article has been cited by 7 ACS Journal articles (5 most recent appear below).

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  Oxidative Conversion of Silyl Enol Ethers to α,β-Unsaturated Ketones Employing Oxoammonium Salts

  Masaki Hayashi, Masatoshi Shibuya, and Yoshiharu Iwabuchi
  Organic Letters2012 14 (1), 154-157

  • Oxidative Conversion of Silyl Enol Ethers to α,β-Unsaturated Ketones Employing Oxoammonium Salts

    Masaki Hayashi, Masatoshi Shibuya, and Yoshiharu Iwabuchi
    Organic Letters2012 14 (1), 154-157

    The oxidative conversion of silyl enol ethers to α,β-unsaturated ketones using a less-hindered class of oxoammonium salts (AZADO+BF4–) is described. The reaction proceeds via the ene-like addition of oxoammonium salts to silyl enol ethers.

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Electron Transfer between [Au₂₅(SC₂H₄Ph)₁₈]⁻TOA⁺ and Oxoammonium Cations

  Zhao Liu , Man-Zhou Zhu , Xiangming Meng , Guoyong Xu , and Rongchao Jin
  The Journal of Physical Chemistry Letters 0 (ja),

  • Electron Transfer between [Au₂₅(SC₂H₄Ph)₁₈]⁻TOA⁺ and Oxoammonium Cations

    Zhao Liu , Man-Zhou Zhu , Xiangming Meng , Guoyong Xu , and Rongchao Jin
    The Journal of Physical Chemistry Letters 0 (ja),

    We report intermolecular electron transfer between 2, 2, 6, 6-tetramethylpiperidin-1-oxoammonium tetrafluoroborate (TEMPO+BF4-) and thiol-stabilized [Au25(SC2H4Ph)18]-TOA+ (abbreviated as Au25-) nanoclusters. The TEMPO+ cations are generated by single ...

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• 

  Making Mixtures to Solve Structures: Structural Elucidation via Combinatorial Synthesis

  Nigel A. Lengkeek, Paul F. Greenwood, Blake Nguyen, George A. Koutsantonis and Matthew J. Piggott
  Journal of Combinatorial Chemistry2010 12 (1), 141-150

  • Making Mixtures to Solve Structures: Structural Elucidation via Combinatorial Synthesis

    Nigel A. Lengkeek, Paul F. Greenwood, Blake Nguyen, George A. Koutsantonis and Matthew J. Piggott
    Journal of Combinatorial Chemistry2010 12 (1), 141-150

    A domino Horner−Wadsworth−Emmons olefination strategy has been used to prepare homologous series of (polyen)ones, and through combinatorial elaboration, corresponding families of highly branched hydrocarbons. Gas chromatography−mass spectrometry of the ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  IBS-Catalyzed Oxidative Rearrangement of Tertiary Allylic Alcohols to Enones with Oxone

  Muhammet Uyanik, Ryota Fukatsu and Kazuaki Ishihara
  Organic Letters2009 11 (15), 3470-3473

  • IBS-Catalyzed Oxidative Rearrangement of Tertiary Allylic Alcohols to Enones with Oxone

    Muhammet Uyanik, Ryota Fukatsu and Kazuaki Ishihara
    Organic Letters2009 11 (15), 3470-3473

    A 2-iodoxybenzenesulfonic acid (IBS)-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with powdered Oxone in the presence of potassium carbonate and tetrabutylammonium hydrogen sulfate has been developed.

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• 

  An Expeditious Entry to 9-Azabicyclo[3.3.1]nonane N-Oxyl (ABNO): Another Highly Active Organocatalyst for Oxidation of Alcohols

  Masatoshi Shibuya, Masaki Tomizawa, Yusuke Sasano and Yoshiharu Iwabuchi
  The Journal of Organic Chemistry2009 74 (12), 4619-4622

  • An Expeditious Entry to 9-Azabicyclo[3.3.1]nonane N-Oxyl (ABNO): Another Highly Active Organocatalyst for Oxidation of Alcohols

    Masatoshi Shibuya, Masaki Tomizawa, Yusuke Sasano and Yoshiharu Iwabuchi
    The Journal of Organic Chemistry2009 74 (12), 4619-4622

    A practical, three-step synthetic route to 9-azabicyclo[3.3.1]nonane N-oxyl (ABNO, 3), an unhindered, stable class of nitroxyl radical, has been developed. ABNO exhibits a highly active nature compared with TEMPO in the catalytic oxidation of alcohols ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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