Abstract
tert-Butyl hydroperoxide in the presence of aluminum and titanium tert-butylates oxidizes phenylalkenes to carbonyl compounds, as well as unsaturated alcohols and their epoxidation products; the process involves free radicals. Organometallic peroxides take an active part in the formation of secondary oxidation products.
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REFERENCES
Stepovik, L.P., Zaburdaeva, E.A., and Dodonov, V.A., Zh. Obshch. Khim., 1997, vol. 67, no. 1, pp. 116-120.
Stepovik, L.P., Martynova, I.M., and Dodonov, V.A., Zh. Obshch. Khim., 2000, vol. 70, no. 8, pp. 1399-1400.
Martynova, I.M., Stepovik, L.P., and Dodonov, V.A., Zh. Obshch. Khim., 2001, vol. 71, no. 5, pp. 785-790.
Finn, M.G. and Sharpless, K.B., J. Am. Chem. Soc., 1991, vol. 113, no. 1, pp. 113-126.
Brendes, D. and Jacobsen, E., J. Org. Chem., 1994, vol. 59, no. 16, pp. 4378-4380.
Tolstikov, G.A., Reaktsii gidroperekisnogo okisleniya (Reactions of Hydroperoxide Oxidation), Moscow: Nauka, 1976, p. 195.
March, J., Advanced Organic Chemistry, New York: Wiley, 1985. Translated under the title Organicheskaya khimiya, Moscow: Mir, 1987, vol. 3, p. 227.
Dodonov, V.A., Stepovik, L.P., Soskova, A.S., and Zaburdaeva, E.A., Zh. Obshch. Khim., 1994, vol. 64, no. 10, pp. 1715-1721.
Stepovik, L.P., Zaburdaeva, E.A., and Dodonov, V.A., Zh. Obshch. Khim., 1997, vol. 67, no. 7, pp. 1173-1178.
Zaburdaeva, E.A., Cand. Sci. (Chem.) Dissertation, Nizhny Novgorod, 1998.
Stepovik, L.P., Zaburdaeva, E.A., and Dodonov, V.A., Zh. Obshch. Khim., 1997, vol. 67, no. 2, pp. 282-287.
Stepovik, L.P., Dodonov, V.A., and Smyslova, G.N., Zh. Obshch. Khim., 1992, vol. 62, no. 1, pp. 123-128.
Dodonov, V.A., Stepovik, L.P., Sofronova, S.M., and Grishin, D.F., Zh. Obshch. Khim., 1983, vol. 53, no. 11, pp. 2534-2536.
Takai, K., Oshima, K., and Nozaki, H., Bull. Chem. Soc. Jpn., 1983, vol. 56, no. 12, pp. 3791-3795.
Takai, K., Oshima, K., and Nozaki, H., Tetrahedron Lett., 1980, vol. 21, no. 17, pp. 1657-1660.
Adam, W., Braun, M., Grilsbeck, A., Lucchini, V., Staab, E., and Will, B., J. Am. Chem. Soc., 1989, vol. 111, no. 1, pp. 203-212.
Bauer, K.H.,Die organische Analuse, Leipzig: Geest and Portig, 1950. Translated under the title Analiz organicheskikh soedinenii, Moscow: Inostrannaya Literatura, 1953, p. 234.
Polyanskii, N.G. and Safronenko, E.D., Zh. Prikl. Khim., 1961, vol. 34, no. 6, pp. 1376-1378.
Stepovik, L.P., Martynova, I.M., and Dodonov, V.A., Zh. Obshch. Khim., 1999, vol. 69, no. 2, pp. 267-272.
Maslennikov, V.P. and Shushunov, V.A., Uspekhi khimii perekisnykh soedinenii i autooksileniya (Progress in Chemistry of Peroxides and Autooxidation), Moscow: Khimiya, 1969, pp. 184-191.
Organic Syntheses, New York: Wiley, 1940-1945, vols. 20–25. Translated under the title Sintezy organicheskikh preparatov, Moscow: Inostrannaya Literatura, 1952, vol. 3, pp. 119-121.
Feld, R. and Cowe, P., The Organic Chemistry of Titanium, London: Butterworth, 1965. Translated under the title Organicheskaya khimiya titana, Moscow: Mir, 1969, p. 263.
Yur'ev, Yu.K., Prakticheskie raboty po organicheskoi khimii (Manual on Organic Chemistry), Moscow: Mosk. Gos. Univ., 1961, p. 295.
Preparative Methods in Polymer Chemistry, Sorenson, W.R. and Campbell, T.W., Eds., New York: Interscience, 1961. Translated under the title Preparativnye metody khimii polimerov, Moscow: Inostrannaya Literatura, 1963, p. 255.
Dictionary of Organic Compounds, Heilbron, I. and Burnbury, H.M., Eds., London: Eyre and Spottiswoode, 1946. Translated under the title Slovar' organicheskikh soedinenii, Moscow: Inostrannaya Literatura, 1949, vol. 1, p. 48; vol. 3, p. 389.
Mannich, G. and Heilner, G., Ber., 1922, vol. 55, no. 2, pp. 356-365.
Weygand, C., Organisch-Chemische Experimentierkunst, Leipzig: Barth, 1943. Translated under the title Metody eksperimenta v organicheskoi khimii, Moscow: Inostrannaya Literatura, 1950, part 2, p. 165.
Razuvaev, G.A., Stepovik, L.P., and Mitrofanova, E.V., Zh. Obshch. Khim., 1965, vol. 35, no. 6, pp. 1095-1098.
Shriner, R., Fuson, R., and Curtin, D., Systematic Identification of Organic Compounds, New York: Wiley, 1980. Translated under the title Identifikatsiya organicheskikh soedinenii, Moscow: Mir, 1983, p. 183.
Pohloudek-Fabini, R. and Beyrich, Th., Organische Analyse unter besonderer Berucksichtigung von Arzneistoffen, Leipzig: Geest and Portig, 1975. Translated under the title Organicheskii analiz, Leningrad: Khimiya, 1981, p. 103.
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Martynova, I.M., Stepovik, L.P. & Dodonov, V.A. Low-Temperature Oxidation of Phenylalkenes with tert-Butyl Hydroperoxide in the Presence of Aluminum and Titanium tert-Butylates. Russian Journal of General Chemistry 71, 1593–1597 (2001). https://doi.org/10.1023/A:1013911322179
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DOI: https://doi.org/10.1023/A:1013911322179