Conclusions
-
1.
The vinylation of sulfur analogs of ethylene glycol and diethylene glycol is accompanied by competing processes: a) the cleavage of the C-S bond (2,2′-thiodiethanol, 2,2′-thiodiethanethiol); b) alkylthioation leading to polyethylene sulfide (1,2-ethanedithiol, 2,2′-thiodiethanethiol); c) condensation at the thiol group with liberation of hydrogen sulfide and formation of the corresponding organic sulfide (1,2-ethanedithiol).
-
2.
The cleavage of the C-S bond in the thioglycols studied under vinylation conditions goes with the participation of acetylene. The probable mechanism of the interaction of the sulfide bridge with the acetylenic bond is discussed.
-
3.
Conditions are developed for the synthesis of S-vinyl derivatives of dithiols.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
M. F. Shostakovskii, E. N. Prilezhaeva, and N. I. Uvarova, Izv. AN SSSR, Otd. khim. n.,1958, 1245.
R. C. Morris and G. W. Conhkin, U.S. Patent 2,664,414, September 29, 1953; Chem. Abstrs.,48, 12789d (1954).
R. D. Yakubov, I. N. Azerbaev, A. S. Atavin, B. A. Trofimov, and V. E. Naumenko, Vestn. ANKazSSR,7, 21 (1963).
M. F. Shostakovskii, A. S. Atavin, and B. A. Trofimov, Zh. obshch. khimii,34, 2112 (1964).
A. S. Atavin, B. A. Trofimov, and V. I. Lavrov, Zh. Vses. khim. obshch. im. D. I. Mendeleeva,10, 119 (1965).
M. F. Shostakovskii, A. S. Atavin, B. V. Prokop'ev, B. A. Trofimov, V. I. Lavrov, and N. M. Deriglazov, Izv. AN SSSR, Ser. khim.,1965, 1485; Dokl. AN SSSR,163, 1412 (1965).
M. F. Shostakovskii, A. S. Atavin, S. V. Amosova, and B. A. Trofimov, Izv. AN SSSR, Ser. khim.,1966, 554.
T. F. Doumani, U.S. Patent 2,402,878, 1946; Chem. Abstrs.,40, 6496 (1946).
T. F. Doumani, U.S. Patent 2,532,612, 1950; Chem. Abstrs.,45, 3868 (1951).
A. L. Kranzfelder and R. R. Vogt, J. Amer. Chem. Soc,60, 1714 (1938).
N. N. Dolgopolov, N. N. Mel'nikov, and S. S. Nametkin, Zh. prikl. khimii,20, 486 (1947).
M. F. Shostakovskii and E. N. Prilezhaeva, Izv. AN SSSR, Otd. khim. n.,1954, 517.
M. F. Shostakovskii, E. N. Prilezhaeva, and N. L Uvarova, Izv. AN SSSR, Otd. khim. n.,1955, 906.
M. F. Shostakovskii, E. N. Prilezhaeva, and N. I. Uvarova, Izv. AN SSSR, Otd. khim. n.,1954, 526.
M. F. Shostakovskii and E. N. Prilezhaeva, Izv. AN SSSR, Otd. khim. n.,1954, 522.
M. F. Shostakovskii, Vinyl Ethers [in Russian], Izd. AN SSSR, Moscow (1952).
P. Sabatier and A. Mailhe, Compt. rend.,150, 1569 (1910).
E. C. Billheimer and E. E. Reid, J. Amer. Chem. Soc.,52, 4338 (1930).
A. Kh. Khomenko, Izv. AN SSSR, Otd. khim. n.,1951, 280.
D. M. Jones and N. F. Wood, J. Chem. Soc.,1965, 1560.
Author information
Authors and Affiliations
Additional information
This article is published in accordance with a resolution of the Conference of Editors-in Chief of Journals of the Academy of Sciences of the USSR, of July 12, 1962, as a dissertation paper by S. V. Amosova.
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 619–623, March, 1967.
Rights and permissions
About this article
Cite this article
Amosova, S.V., Atavin, A.S. & Trofimov, B.A. Some sulfur analogs of ethylene glycol and diethylene glycol in the vinylation reaction. Russ Chem Bull 16, 596–600 (1967). https://doi.org/10.1007/BF00906000
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00906000