Abstract
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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References
Fodor, G., and Kiss, J., Nature, 163, 287 (1949).
Fodor, G., Lecture delivered at the Meeting of Hung. Engineers Union Szeged, Dec. 12, 1948; summarized in Acta Chem. Phys. Szeged, 2, 227 (1949).
Raiford, L., and Mortensen, F., could not initiate acyl migration of bis-acylated 2-amino-cyclohexanol (J. Amer. Chiem. Soc., 50, 1201; 1928).
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).
English Patent 454,042 (1936).
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).
Beilstein, 13, 348, 4th edit.
Welsh, L. H., J. Amer. Chem. Soc., 69, 128 (1947).
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).
Hückel, W., "Theoret. Grundl. d. org. Chemie", 74 (3rd edit.).
Bier, G., Experientia, 2, 82 (1946).
Gilman, "Organic Chemistry", 109 (2nd edit.).
Hückel, W., loc. cit., 71.
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FODOR, G., KISS, J. Configuration of Alicyclic Amino-Alcohols. Nature 164, 917–918 (1949). https://doi.org/10.1038/164917a0
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DOI: https://doi.org/10.1038/164917a0
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