Beckmann Rearrangement of Ketoximes to Lactams by Triphosphazene Catalyst^†

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Abstract

Triphosphazene, 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-chloride (TAPC), was found to be an efficient catalyst for the Beckmann rearrangement of cyclohexanone oxime and cyclododecanone oxime to ε-caprolactam and laurolactam, which are raw materials of nylon-6 and nylon-12, respectively.

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This article has been cited by 8 ACS Journal articles (5 most recent appear below).

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  Copper-Catalyzed Coupling of Oxime Acetates with Aldehydes: A New Strategy for Synthesis of Pyridines

  Zhi-Hui Ren, Zhi-Yuan Zhang, Bing-Qin Yang, Yao-Yu Wang, and Zheng-Hui Guan
  Organic Letters2011 13 (19), 5394-5397

  • Copper-Catalyzed Coupling of Oxime Acetates with Aldehydes: A New Strategy for Synthesis of Pyridines

    Zhi-Hui Ren, Zhi-Yuan Zhang, Bing-Qin Yang, Yao-Yu Wang, and Zheng-Hui Guan
    Organic Letters2011 13 (19), 5394-5397

    Copper-catalyzed coupling of oxime acetates with aldehydes offers a new strategy for the synthesis of highly substituted pyridines. This novel method tolerates a wide range of functionality and allows for rapid elaboration of the oxime acetates into a ...

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

  Influence of the Structure of Polyfluorinated Alcohols on Brønsted Acidity/Hydrogen-Bond Donor Ability and Consequences on the Promoter Effect

  Daniela Vuluga, Julien Legros, Benoit Crousse, Alexandra M. Z. Slawin, Christian Laurence, Pierre Nicolet, and Danièle Bonnet-Delpon
  The Journal of Organic Chemistry2011 76 (4), 1126-1133

  • Influence of the Structure of Polyfluorinated Alcohols on Brønsted Acidity/Hydrogen-Bond Donor Ability and Consequences on the Promoter Effect

    Daniela Vuluga, Julien Legros, Benoit Crousse, Alexandra M. Z. Slawin, Christian Laurence, Pierre Nicolet, and Danièle Bonnet-Delpon
    The Journal of Organic Chemistry2011 76 (4), 1126-1133

    The influence of substituents on the properties of tri- and hexafluorinated alcohols derived from 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) was examined. Measurements of specific solvent−solute interactions revealed that H-...

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

  TAPC-Promoted Oxidation of Sulfides and Deoxygenation of Sulfoxides

  Kiumars Bahrami, Mohammad M. Khodaei, and Mehdi Sheikh Arabi
  The Journal of Organic Chemistry2010 75 (18), 6208-6213

  • TAPC-Promoted Oxidation of Sulfides and Deoxygenation of Sulfoxides

    Kiumars Bahrami, Mohammad M. Khodaei, and Mehdi Sheikh Arabi
    The Journal of Organic Chemistry2010 75 (18), 6208-6213

    1,3,5-Triazo-2,4,6-triphosphorine-2,2,4,4,6,6-tetrachloride (TAPC) was found to be an efficient promoter for the oxidation of sulfides and deoxygenation of sulfoxides. Excellent yields, short reaction time, easy and quick isolation of the products, ...

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

  Multicatalytic One-Pot Reaction of 1-(2-Alkynylphenyl)ketoximes for Generation of Indole Derivatives

  Guanyinsheng Qiu, Qiuping Ding, Hui Ren, Yiyuan Peng, and Jie Wu
  Organic Letters2010 12 (18), 3975-3977

  • Multicatalytic One-Pot Reaction of 1-(2-Alkynylphenyl)ketoximes for Generation of Indole Derivatives

    Guanyinsheng Qiu, Qiuping Ding, Hui Ren, Yiyuan Peng, and Jie Wu
    Organic Letters2010 12 (18), 3975-3977

    Multicatalytic one-pot Beckmann rearrangement/intramolecular cyclization/halogenation reaction of 1-(2-alkynylphenyl)ketoxime is reported, leading to the expected indole derivatives in good yield.

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

  Direct Amide Synthesis from Either Alcohols or Aldehydes with Amines: Activity of Ru(II) Hydride and Ru(0) Complexes

  Senthilkumar Muthaiah, Subhash Chandra Ghosh, Joo-Eun Jee, Cheng Chen, Jian Zhang and Soon Hyeok Hong
  The Journal of Organic Chemistry2010 75 (9), 3002-3006

  • Direct Amide Synthesis from Either Alcohols or Aldehydes with Amines: Activity of Ru(II) Hydride and Ru(0) Complexes

    Senthilkumar Muthaiah, Subhash Chandra Ghosh, Joo-Eun Jee, Cheng Chen, Jian Zhang and Soon Hyeok Hong
    The Journal of Organic Chemistry2010 75 (9), 3002-3006

    An in situ generated catalyst from readily available RuH2(PPh3)4, an N-heterocyclic carbene (NHC) precursor, NaH, and acetonitrile was developed. The catalyst showed high activity for the amide synthesis directly from either alcohols or aldehydes with ...

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

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