Web of Science (Emerging Sources Citation Index)

Document Type : Original Research Article


Department of Chemistry, Chemical Institute of Kazan Federal University, Russia


Secondary dialkyl-, diaryl-, alkylarylarsinghalides hold one of the most important places in the hierarchy of various classes of organo-arsenic compounds. These compounds can serve as a key for accessing the synthesis of tertiary arsines, studying their structure, reactivity, stereochemical and biological properties. Secondary substituted mixed alkylarylarsinghalides, due to the active halogen atom associated with arsenic, have high reactivity in various chemical substitution reactions. Accordingly, they are a source for obtaining representatives of the next series of organo-arsenic compounds with useful properties to meet the needs of various areas of production. Despite the significant position in the chemistry of organo-arsenic compounds, these substances remain poorly studied and therefore the problem of their study still remains relevant. This work is devoted to the study of literary sources that describe methods for the synthesis of secondary arsinghalides, including the experimental results of the author's research. Based on the analysis of the data obtained, the authors recommend the method he has tested for the synthesis of secondary asymmetric arsinghalides. The work provides a detailed description of the recommended method for the synthesis of ethylarylarsine chlorides and gives comparative characteristics of a number of obtained substances, as well as the results of analytical and spectroscopic studies, confirming their compliance with the accepted structures.

Graphical Abstract

Methods for synthesis of secondary alkylarylarsinechlorides and their reactivity


Main Subjects

[1] W.G. Lowe, С.S. Hamilton, J. Am. Chem. Soc.,1935, 57, 2314-2317.

[2] W.W. Beck, С.S. Hamilton, J. Am. Chem. Soc., 1939, 60, 620-624.

[3] G. Salem, S.B. Wild, J. Organomet. Chem1989, 370, 33-41.

[4] T.F. Winmill, J. Chem. Soc. Faraday Trans1912, 101, 718-725.

[5] J.B. Lambert, D.H. Johnson, J. Am. Chem. Soc.1968, 90, 1349-1350.

[6] J.B. Lambert, G.F. Jackson, J. Am. Chem. Soc., 1968, 90, 1350-1351.

[7] S.L. Lawton, C.J. Fuhrmeister, R.G. Haas, C.S. Jarman, F.G. Lohmeyer, Inorg. Chem1974, 13, 135-143.
[8] G.T. Morgan, D.C. Vining, J. Chem. Soc. Faraday Trans, 1920, 117, 777-783.

[9] W.M. Dehn, S.J. Mcgrath, J. Am. Chem. Soc., 1906, 28, 347-361.

[10] G.J. Burrows, A. Lench, J. proc. R. Soc. N.S.W., 1936, 70, 294-299.

[11] L.B. Ionov, V.I. Kornev, L.A. Kunitskaya, Chem. Inform.1976, 7, 93-98.

[12] P.W. Lee, T.R. Omstead, D.R. McKenna, K.F. Jensen, J. Cryst. Growth1988, 93, 134-142.

[13] W.R. Cullen, D.S. Dawson, G.E. Styan, J. Organomet. Chem, 1965, 3, 406-413.

[14] W.R. Cullen, F.S. Dawson, G.E. Styan, Canad. J. Chem, 1965, 43, 3392-3399.

[15] F.G. Mann, B.B. Smith, J. Chem. Soc., 1952, 63, 4544-4545.

[16] F.G. Mann, R.C. Cookson, Nature1946, 157, 846-846.

[17] W.H. Mills, R. Raper, J. Chem. Soc. Faraday Trans, 1925, 127, 2479-2483.

[18] T.N. Polynova, M.A. Porai-Koshits, J. Struct. Chem.1967, 7, 147-169.

[19] G. Kamai, G.M. Usacheva, Russ. Chem. Rev1966, 35, 601-612.