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Mechanism of the Rearrangement of Quinamine to IsoQuinamine

Naturevolume 166pages105106 (1950) | Download Citation



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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  1. 1

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

  2. 2

    Kirby, J. Chem. Soc., 528 (1945). Goutarel, Janot, Prelog and Taylor, Helv. Chim. Acta, 33, 150 (1950). Bendz, Miss G., Culvenor, Goldsworthy, Kirby and Robinson ; Paul Karrer Festschrift, Zurich (1949); J. Chem. Soc. (in the press, 1950).

  3. 3

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

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  1. Dyson Perrins Laboratory, University of Oxford

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


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