Abstract
IN the preparation of the disulphide of 2-(2-mercapto-ethylamino)-2-oxazoline from 2-methylthio-2-oxazoline and 2-mercaptoethylamine hydrochloride, an intermediate with anomalous properties was encountered1. The properties of the intermediate, C5H10N2OS, were not consistent with its formulation as the ancitipated 2-(2-mercapto-ethylamino)-2-oxazoline (I), and spectroscopic evidence (infra-red and nuclear magnetic resonance spectra) suggested the possibility that the novel heterocyclic spiran (II) had been obtained. In order to establish the structure of this anomalous intermediate unambiguously, we undertook an X-ray crystal-structure analysis. 
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
Clapp, R. C., Long, L., jun., and Hasselstrom, T., J. Org. Chem., 28, 1308 (1963).
Robertson, J. H., and Beevers, C. A., Acta Cryst., 4, 270 (1951).
McCallum, G. H., Robertson, J. M., and Sim, G. A., Nature, 184, 1863 (1959).
Hughes, E. W., Yakel, H. L., and Freeman, H. C., Acta Cryst., 14, 345 (1961).
Sutor, D. J., Acta Cryst., 11, 83 (1958).
Schomaker, V., and Pauling, L., J. Amer. Chem. Soc., 61, 1769 (1939).
Cox, E. G., Gillot, R. J. J. M., and Jeffrey, G. A., Acta Cryst., 2, 356 (1949).
Bak, B., Christensen, D., Dixon, W. B., Hansen-Nygaard, L., Andersen, J. R., and Schottländer, M., J. Mol. Spectroscopy, 9, 124 (1962).
Burrus, C. A., and Gordy, W., Phys. Rev., 91, 313 (1953).
See, inter alia, Paul, I. C., Sim, G. A., Hamor, T. A., and Robertson, J. M., J. Chem. Soc., 4133 (1962). Hamilton, J. A., Hamor, T. A., Robertson, J. M., and Sim, G. A., J. Chem. Soc., 5061 (1962). Donohue, J., and Trueblood, K., Acta Cryst., 5, 419 (1952).
Tables of Interatomic Distances and Configuration in Molecules and Ions, Chem. Soc. Special Publ., No. 11 (1958).
Pauling, L., The Nature of the Chemical Bond (Cornell University Press, Ithaca, 1948).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
MILLER, R., MONTEATH ROBERTSON, J., SIM, G. et al. Structure of an Anomalous Heterocyclic Intermediate. Nature 202, 287–288 (1964). https://doi.org/10.1038/202287a0
Issue Date:
DOI: https://doi.org/10.1038/202287a0
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.
