Summary
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1.
β-Chloroethylmethylarylamides of dialkylphosphoric acids were obtained by addition of halogenated hydrocarbons to ethyleneamides of dialkylphosphoric acids. The addition reaction is shown to proceed with rupture of the ring.
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2.
Addition of chlorine to ethyleneamides of dialkylphosphoric acids gave a series of β-chloroethylchloramides of dialkylphosphoric acids.
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3.
It is shown: a) that the synthesized chloramides undergo the Arbuzov rearrangement in the normal direction; b) the chloramides add on to ethyleneamides of dialkylphosphoric acids with formation of symmetrical bisdi-alkylphosphono-di-β-chloroethylhydrazines.
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Literature Cited
N. P. Grechkin, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1956, 538.
P. Lasselle and S. Sundet, J. Am. Chem. Soc. 63, 2374 (1941).
N. Kreutzkamp and H. Kayser, Naturwissenschaften 42, 14, 415 (1955).
B. A. Arbuzov, P. L. Alimov, and O. N. Fedorova, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1956, 932.
G. Goldschmidt and R. Jahoda, Monatsh. 12, 83 (1891).
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Grechkin, N.P. Organophosphorus derivatives of ethylenemine 2. Addition to dialkylphosphorousacid-ethyl eneamides of halogenated hydrocarbons and of halogens. Russ Chem Bull 6, 1084–1088 (1957). https://doi.org/10.1007/BF01169385
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DOI: https://doi.org/10.1007/BF01169385