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Mechanism of the Fischer Indole Synthesis

Abstract

THE mechanism previously proposed1,2 for the Fischer indole reaction has assumed that the intermediate stages involve an o-benzidine-type re-arrangement. This may be illustrated as follows, considering, as an example, the phenyl hydrazone of cyclohex-anone :

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References

  1. Robinson and Robinson, J. Chem. Soc., 113, 639 (1918); 125, 827 (1924).

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  2. Allen and Wilson, J. Amer. Chem. Soc., 65, 611 (1943).

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  3. Ingold and Kidd, J. Chem. Soc., 984 (1933).

  4. Pausacker and Robinson, J. Chem. Soc., 1557 (1947).

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PAUSACKER, K., SCHUBERT, C. Mechanism of the Fischer Indole Synthesis. Nature 163, 289–290 (1949). https://doi.org/10.1038/163289c0

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