Conclusions
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1.
The ratio of the rate constants of the interaction of triethyl phosphite with isopropyl iodide and the simultaneous parallel-successive isomerization of triethyl phosphite was determined. At 100° in toluene solution and a pressure of 4000 kg/cm2, the rate constant of the first sterically hindered reaction is approximately 60 times lower than the rate constant of the second reaction.
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2.
The interaction of triethyl phosphite with tert-butyl chloride at the temperatures 100–200° and pressures up to 12,000 kg/cm2 does not lead to the formation of the diethyl ester of tert-butylphosphinic acid. Diethyl esters of phosphorous and ethylphosphinic acids, ethyl chloride, isobutylene, its dimers and trimers, and higher molecular products of secondary reactions were found in the reaction products.
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Literature cited
M. G. Gonikberg and I. Z. Fainshtein, Dokl. AN SSSR,147, 612 (1962).
M. G. Gonikberg and I. Z. Fainshtein, Izv. AN SSSR. Ser. Khim.,1965, 1469.
C. Walling and J. Pellon, J. Amer. Chem. Soc.,79. 4776 (1957).
A. E. Arbuzov and L. V. Nesterov, Dokl. AN SSSR,92, 57 (1953).
I. Z. Fainshtein and M. G. Gonikberg, Izv. AN SSSR. Ser. Khim.,1964, 1401.
G. Aksnes and D. Aksnes, Acta Chem. Scand.,17, No. 7, 2121 (1963);18, No. 1, 38 (1964).
F. C. Buck and T. Yoke, J. Organ. Chem.,27, No. 10, 3675 (1962).
V. M. Zhulin, M. G. Gonikberg, and V. N. Zagorbinina, Izv. AN SSSR. Otd. Khim. N.,1962, 716.
W. Strecker and R. Spitaler, Ber.,59, 1773 (1926).
A. E. Arbuzov and A. A. Ivanov, Zh. Russk. Fiz.-Khim. Obshch.,47, 2019 (1915).
V. P. Butuzov, G. P. Shakhovskoi, and G. M. Gonikberg, Transactions of the Institute of Crystallography, Academy of Sciences of the USSR [in Russian], No. 11 (1955), p. 233.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 533–536, March, 1967.
We should like to express our sincere gratitude to A. D. Snegova for performing the chromatographic investigation of fraction I.
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Gonikberg, M.G., Fainshtein, I.Z. Interaction of triethyl phosphite with isopropyl iodide and tert-butyl chloride at high pressures. Russ Chem Bull 16, 516–519 (1967). https://doi.org/10.1007/BF00905983
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DOI: https://doi.org/10.1007/BF00905983