Abstract
In the synthesis of 3-methyl-2,3-epoxypent-4-yne by the action of powdered caustic potash on 4-chloro-3-methylpent-1-yn-3-ol, a mixture of cis and trans oxides is formed with predominance of the isomer to which, on the basis of the PMR spectroscopy of saturated and acetylenic α-oxides, the cis configuration of the methyl groups has been ascribed.
Similar content being viewed by others
Literature cited
M. H. Gianni, E. L. Stogryn, and C. M. Orlando, J. Phys. Chem., 67, 1385 (1963).
G. Allen, D. J. Blears, and K. H. Webb, J. Chem. Soc., 810 (1965).
A. T. Bottini and R. L. Van Etten, J. Org. Chem., 30, 2994 (1965).
G. G. Lyle and L. K. Keefer, J. Org. Chem., 31, 3921 (1966).
L. Bellamy, Infrared Spectra of Complex Molecules, 2nd ed., Methuen, London (1958).
K. S. Mingaleva, K. G. Golodova, and A. A. Petrov, Zh. Organ. Khim., 1, 2078 (1965).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 19–21, January, 1974.
Rights and permissions
About this article
Cite this article
Golodova, K.G., Yakimovich, S.I. An investigation in the field of the stereochemistry of acetylenic α oxides. Chem Heterocycl Compd 10, 14–16 (1974). https://doi.org/10.1007/BF00475898
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00475898