Letter | Published:

Mechanism of the Rearrangement of Quinamine to IsoQuinamine

Nature volume 166, pages 105106 (15 July 1950) | Download Citation

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Abstract

THE transformation of quinamine to isoquinamine is brought about by the action of hot isoamyl alcoholic sodium isoamyloxide on quinamine1. (We have found that, under milder conditions with ethanolic sodium ethoxide, the alkaloid is first epimerized with partial formation of epiquinamine, almost certainly identical with conquinamine.)

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References

  1. 1.

    , J. Chem. Soc., 735 (1949).

  2. 2.

    , J. Chem. Soc., 528 (1945). , , and , Helv. Chim. Acta, 33, 150 (1950). , , , and ; Paul Karrer Festschrift, Zurich (1949); J. Chem. Soc. (in the press, 1950).

  3. 3.

    and , Nature, 165, 36 (1950). cf. , J. Amer. Chem. Soc., 72, 614 (1950).

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Affiliations

  1. Dyson Perrins Laboratory, University of Oxford. March 13.

    • C. C. J. CULVENOR
    • , L. J. GOLDSWORTHY
    • , K. S. KIRBY
    •  & R. ROBINSON

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https://doi.org/10.1038/166105a0

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