Summary
The formation of the acetic esters of tri- and di-bromo ketols by the action of HOBr on the acetic esters of secondary and tertiary acetylenic alcohols is due to the particularly strongly protonized (acidic) hydrogen atom of the methylidyne group=C-H, which results from profound frequency modulation of the vibrations of the latter by the low-frequency intermolecular vibrations at the hydrogen bonds.
Similar content being viewed by others
Literature cited
A. A. Akhrem, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk 693 (1960).
M I. Batuev and A. D. Matveeva, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk, 448 (1951).
M. I. Batuev, Zhur. Obshch Khim.26, 1888 (1956); Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk 1329 (1956). Zhur. Obshch. Khim.28, 2903 (1958); M. I. Batuev and A. D. Matveeva, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk 1393 (1958); M. I. Batuev, A. D. Petrov, V. a. Ponomarenko, and A. d. Matveeva, ibid.,1070, 1243 (1956).
M. J. Copley and C. E. Holley, J. Am. Chem. Soc.61, 1599 (1939); J A. Nieuwland and R. R. Vogt, Chemistry of Acetylene [Russian translation] (Moscow, 1947).
M. I. Batuev, Zhur, Fiz. Khim.23, 1399 (1949);24, 381 (1950);21, 137 (1947);25, 884 (1951); Izvest. Akad. Nauk SSSR, Ser. Fiz.11, 336 (1947);14, 429 (1950):
S. N. Andreev and T. G. Balicheva, Doklady Akad. Nauk SSSR90, 149 (1953).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Batuev, M.I., Akhrem, A.A. & Matveeva, A.D. Raman-spectrum investigation of some acetylenic alcohols and their acetic esters. Russ Chem Bull 9, 2037–2042 (1960). https://doi.org/10.1007/BF00912058
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00912058