Mechanism of the Beckmann Rearrangement


THE recent resurgence of interest in the mechanism of the Beckmann change reflects the perennial fascination which this subject has for chemists. First, Higman1 and LeFevre2 have suggested that the cation (I) rearranges by rotation of the central pair <C=N> through 90° to form (II).

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  1. 1

    Higman, Nature, 156, 242 (1945).

  2. 2

    LeFevre, J. Soc. Chem. Ind., 49, 391 (1945).

  3. 3

    Dewar, Nature, 156, 688 (1945).

  4. 4

    For summary and references, see Brynmor Jones, Chem. Rev., 35, 335 (1945).

  5. 5

    Brodsky and Micluchin., C.R. Acad. Sci. U.S.S.R., 32, 558 (1941). J. Chem. Phys., 11, 342 (1943).

  6. 6

    Campbell and Kenyon., J. Soc. Chem. Ind., 49, 391 (1945), and private communication.

  7. 7

    Chapman, private communication.

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JONES, B. Mechanism of the Beckmann Rearrangement. Nature 157, 519 (1946) doi:10.1038/157519a0

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