Abstract
tert-Butyl peroxyacetate, tert-butyl peroxybutyrate, tert-butyl phenylperoxyacetate, and tert-butyl peroxyundecanoate were obtained in nearly quantitative yields by the esterification of the corresponding carboxylic acids with tert-butyl hydroperoxide in the presence of trifluoroacetic anhydride and pyridine in nonaqueous medium at 0–5°C. No tert-butyl peroxytrifluoroacetate was formed as a by-product during the process. A possible reaction mechanism is discussed.
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References
Rakhimov, A.I., Khimiya i tekhnologiya organicheskikh perekisnykh soedinenii (Chemistry and Technology of Organic Peroxy Compounds), Moscow: Khimiya, 1979.
Bratichak, M.M. and Sikors’kii, R.T., Osnovi sintezu i reaktsiinoï zdatnosti visokomolekulyarnikh spoluk (Principles of Synthesis and Reactivity of High-Molecular Compounds), L’viv: Nats. Univ. L’vivska Politekh., 2003.
Bartlett, P.D. and Hiatt, R.R., J. Am. Chem. Soc., 1958, vol. 80, p. 1398; Hock, H., Chem. Ber., 1955, vol. 88, p. 1544; Lorand, O.P. and Bartlett, P.D., J. Am. Chem. Soc., 1966, vol. 88, p. 3294.
Uspekhi khimii organicheskikh perekisnykh soedinenii i autookisleniya (Advances in the Chemistry of Organic Peroxy Compounds and Autooxidation), Emanuel’, N.M., Ed., Moscow: Khimiya, 1969; Pincock, R.E., J. Am. Chem. Soc., 1964, vol. 86, p. 1820; Khimiya perekisnykh soedinenii (Chemistry of Peroxy Compounds), Chernyaev, I.I., Ed., Moscow: Akad. Nauk SSSR, 1963; Ol’dekop, Yu.A., Bylina, G.S., and Buloichik, B.I., Izv. Akad. Nauk BSSR, Ser. Khim., 1970, no. 2, p. 109.
Ruchardt, Ch. and Hecht, H., Chem. Ber., 1964, vol. 97, p. 2716; Lyashenko, O.K., Nesterova, I.P., and Antonovskii, V.L., Khim. Promst., 1974, no. 9, p. 659; UK Patent no. 1072296, 1967; UK Patent no. 1226468, 1971; Pincock, R.E., J. Am. Chem. Soc., 1965, vol. 87, p. 1274.
Antonovskii, V.L. and Lyashenko, O.K., Zh. Org. Khim., 1972, vol. 8, p. 2615.
Hecht, R. and Ruchardt, Ch., Chem. Ber., 1963, vol. 96, p. 1281; Staab, H.A., Rohr, W., and Graf, F., Chem. Ber., 1965, vol. 98, p. 1122.
Parish, R.C. and Stock, L.M., J. Org. Chem., 1965, vol. 30, p. 65.
Zubkov, V.A., Koton, M.M., Kudryavtsev, V.V., and Svetlichnyi, V.M., Zh. Org. Khim., 1980, vol. 16, p. 2486.
Weissberger, A., Proskauer, E.S., Riddick, J.A., and Toops, E.E., Jr., Organic Solvents: Physical Properties and Methods of Purification, New York: Intersci., 1955, 2nd ed.
Milas, N.A. and Surgenor, D., J. Am. Chem. Soc., 1946, vol. 68, p. 642.
Perry, S.G., Amos, R., and Brewer, P.I., Practical Liquid Chromatography, New York: Plenum, 1972. Translated under the title Prakticheskoe rukovodstvo po zhidkostnoi khromatografii, Moscow: Mir, 1974, p. 164.
Antonovskii, V.L. and Buzlanova, M.M., Analiticheskaya khimiya organicheskikh peroksidnykh soedinenii (Analytical Chemistry of Organic Peroxy Compounds), Moscow: Khimiya, 1978.
Antonovskii, V.L., Organicheskie perekisnye initsiatory (Organic Peroxide Initiators), Moscow: Khimiya, 1972.
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Original Russian Text © V.A. Donchak, S.A. Voronov, R.S. Yur’ev, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 4, pp. 505–508.
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Donchak, V.A., Voronov, S.A. & Yur’ev, R.S. New synthesis of tert-butyl peroxycarboxylates. Russ J Org Chem 42, 487–490 (2006). https://doi.org/10.1134/S1070428006040026
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DOI: https://doi.org/10.1134/S1070428006040026