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.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
Similar content being viewed by others
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.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
FODOR, G., KISS, J. Configuration of Alicyclic Amino-Alcohols. Nature 164, 917–918 (1949). https://doi.org/10.1038/164917a0
Issue Date:
DOI: https://doi.org/10.1038/164917a0
This article is cited by
-
Stereochemistry of Cocaine
Nature (1954)
-
Stereochemistry of Tropine and pseudo-Tropine
Nature (1952)
-
Configurational Correlation of Chloramphenicol and of nor-pseudo-Ephedrine
Nature (1951)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.
