A Study of the Formation of Haloamines and Cyclic Amines by the Free Radical Chain Decomposition of N-Haloammonium Ions (Hofmann-Löffler Reaction)1

E. J. Corey, Walter R. Hertler
J. Am. Chem. Soc., 1960, 82 (7), pp 1657–1668
DOI: 10.1021/ja01492a035
Publication Date: April 1960
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This article has been cited by 8 ACS Journal articles (5 most recent appear below).

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    Total Synthesis of (+)-Lyconadin A and Related Compounds via Oxidative C−N Bond Formation

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    Journal of the American Chemical Society2009 131 (31), 11187-11194
    • Total Synthesis of (+)-Lyconadin A and Related Compounds via Oxidative C−N Bond Formation

      Scott P. West, Alakesh Bisai, Andrew D. Lim, Raja R. Narayan and Richmond Sarpong
      Journal of the American Chemical Society2009 131 (31), 11187-11194

      The formation of carbon−nitrogen (C−N) bonds is a fundamental bond construction in organic synthesis and is indispensable for the synthesis of alkaloid natural products. In the context of the synthesis of the architecturally complex Lycopodium alkaloid ...

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    Rearrangemements in Piperidine-Derived Nitrogen-Centered Radicals. A Quantum-Chemical Study

    Valerije Vrček and Hendrik Zipse
    The Journal of Organic Chemistry2009 74 (8), 2947-2957
    • Rearrangemements in Piperidine-Derived Nitrogen-Centered Radicals. A Quantum-Chemical Study

      Valerije Vrček and Hendrik Zipse
      The Journal of Organic Chemistry2009 74 (8), 2947-2957

      Hydrogen migration reactions in piperidine radicals and their protonated counterparts were studied by quantum chemical calculations. G3B3 and G3(MP2)-RAD levels of theory were used as reference procedures in order to evaluate the efficiency of other ...

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    1,3-Diol Synthesis via Controlled, Radical-Mediated C−H Functionalization

    Ke Chen, Jeremy M. Richter and Phil S. Baran
    Journal of the American Chemical Society2008 130 (23), 7247-7249
    • 1,3-Diol Synthesis via Controlled, Radical-Mediated C−H Functionalization

      Ke Chen, Jeremy M. Richter and Phil S. Baran
      Journal of the American Chemical Society2008 130 (23), 7247-7249

      The invention of a method for the synthesis of 1,3-diols from the corresponding alcohols is described, via controlled, radical-mediated C−H functionalization. The sequence described herein entails near quantitative conversion to the corresponding ...

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    δ and α SP3 C−H Bond Oxidation of Sulfonamides with PhI(OAc)2/I2 under Metal-Free Conditions

    Renhua Fan, Dongming Pu, Fengqi Wen, and Jie Wu
    The Journal of Organic Chemistry2007 72 (23), 8994-8997
    • δ and α SP3 C−H Bond Oxidation of Sulfonamides with PhI(OAc)2/I2 under Metal-Free Conditions

      Renhua Fan, Dongming Pu, Fengqi Wen, and Jie Wu
      The Journal of Organic Chemistry2007 72 (23), 8994-8997

      An efficient δ and α sp3 C−H bond oxidation of sulfonamides with PhI(OAc)2/I2 under metal-free conditions has been reported. The reaction provides a useful route to pyrrolidines, N-sulfonylimines, and various sulfonamide derivatives. The potential of this ...

  • Cover Image

    Efficient Method for Selective Introduction of Substituents as C(5) of Isoleucine and Other α-Amino Acids

    Leleti Rajender Reddy, B. V. Subba Reddy, and E. J. Corey
    Organic Letters2006 8 (13), 2819-2821
    • Efficient Method for Selective Introduction of Substituents as C(5) of Isoleucine and Other α-Amino Acids

      Leleti Rajender Reddy, B. V. Subba Reddy, and E. J. Corey
      Organic Letters2006 8 (13), 2819-2821

      A useful process for the position-selective remote bromination of N-trifluoroacetyl-α-amino esters is illustrated for the isoleucine case. The 5-bromoisoleucine derivative shown above can be used for the synthesis of many modified amino acids, as ...

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