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Configuration of Alicyclic Amino-Alcohols


WE have extended our investigations1 on the acyl migration reaction N6666666 O to acyl derivatives of diastereoisomeric alicyclic amino-alcohols2, such as 2-amino-cyclohexanol3, with the view of establishing the relative steric positions4 (that is, configuration) of hydroxyl and acylamido groups.

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  1. Fodor, G., and Kiss, J., Nature, 163, 287 (1949).

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  2. Fodor, G., Lecture delivered at the Meeting of Hung. Engineers Union Szeged, Dec. 12, 1948; summarized in Acta Chem. Phys. Szeged, 2, 227 (1949).

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  3. Raiford, L., and Mortensen, F., could not initiate acyl migration of bis-acylated 2-amino-cyclohexanol (J. Amer. Chiem. Soc., 50, 1201; 1928).

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  4. Attempts to convert amino-cyclohexanol into 1.2-cyclohexandiol of known configuration were unsuccessful: Wilson, N. A. B., and Read, J., J. Chem. Soc., 1270 (1935).

  5. English Patent 454,042 (1936).

  6. McCasland, G. E., et al., J. Amer. Chem. Soc., 71, 638 (1949), found that benzamido-cyclohexanol, m.p. 189°, can be prepared from its diastereoisomer by tosylation and subsequent detosylation in an analogous manner to the preparation of cis-acetyl-cyclohexandiol-1.2 from the trans form. cf. Winstein, S., et al., J. Amer. Chem. Soc., 64, 2796 (1942).

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  8. Welsh, L. H., J. Amer. Chem. Soc., 69, 128 (1947).

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  9. Incomplete acyl migration was recorded in the case of bis-acyl-2-amino-phenol, leading to an equilibrium mixture, cf. le Rosen, A. L., et al., J. Amer. Chem. Soc., 70, 2705 (1948).

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  10. Hückel, W., "Theoret. Grundl. d. org. Chemie", 74 (3rd edit.).

  11. Bier, G., Experientia, 2, 82 (1946).

  12. Gilman, "Organic Chemistry", 109 (2nd edit.).

  13. Hückel, W., loc. cit., 71.

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FODOR, G., KISS, J. Configuration of Alicyclic Amino-Alcohols. Nature 164, 917–918 (1949).

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