Summary
-
1.
By the action of alcohols on ethylphosphonous dichloride in presence of pyridine or triethylamine we have synthesized the following esters, which have not been described previously: the dimethyl, diethyl, dipropyl, diisopropyl, dibutyl, dihexyl, dioctyl, and diphenyl esters of ethylphosphonous acid.
-
2.
Ethylphosphonous esters, being tervalent phosphorus derivatives, readily undergo addition reactions: they combine readily with sulfur, give complex compounds with cuprous iodide, and are very readily oxidized.
-
3.
It has been shown that ethylphosphonous dichloride combines with sulfur in presence of aluminum chloride as catalyst.
-
4.
A study has been made of the rearrangement of ethylphosphonaus esters under the influence of alkyl halides, carbon tetrachloride, ethyl chloxoacetate, and diethylcarbamoyl chloride. The reaction follows the scheme of the A. E. Arbuzov rearrangement.
-
5.
Syntheses have been carried out for the first. time of ethylphosphonothionic esters, dialkylphosphinic esters, ethyltrichloromethylphosphinic esters, (ethoxycarbonylmethyl)ethylphosphinic esters, and diethylamides of alkoxy(ethyl)phosphinylformic acids.
Similar content being viewed by others
Literature cited
A. E. Arbuzov, Dissertation, Kazan (1914); A. E. Arbuzov, J. Russ. Chem. Soc., 42, 395 (1910); A. E. Arbuzov, J. Gen. Chem., 4, 898 (1934); A.E. Arbuzov, Gilm. Kamai, and O. N. Belorossova, J. Gen. Chem., 15, 766 (1945); A. E. Arbuzov and A. I. Razumov, Bull. Acad. Sci. U.S.S.R., Div. Chem. Sci., 167 (1945); Z. L. Khisamova and Gilm Kamai, J. Gen. Chem., 7, 1162 (1950).
Gilm Kamai and E. A. Gerasimova, Trans. Kazan, Chem. Tech. Inst, 15, 26 (1950).
R. B. Fox, J. Am. Chem. Soc. 9, 4147 (1950).
M. S. Kharasch, E. V. Jensen and S. Weinhouse, J. Am. Chem. Soc., 14, 429 (1949).
F. Guichard, Ber., 32, 1572 (1899).
Gilm Kamai and L. P. Egorova, J. Gen. Chem., 16, 1521 (1946); Proc. Acad. Sci. U.S.S.R. 55, 223 (1947) Gilm Kamai J. Gen. Chem., 18, 440 (1948).
A. E. Arbuzov and A. A. Dunin, J. Russ. Chem. Soc., 46, 295 (1914).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Arbuzov, B.A., Rizpolozhensky, N.I. Esters of ethylphosphonous acid, and some of their reactions Communication I. Full esters of ethylphosphonous acid. Russ Chem Bull 1, 765–772 (1952). https://doi.org/10.1007/BF01198862
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01198862