Abstract
The formation of phenol was observed in aqueous alkaline solutions of chlorobenzene. Diphenyl ether was formed in aqueous tert-butanol solutions of chlorobenzene and bromobenzene in the presence of phenoxide ions. An increase in the temperature of irradiation resulted in an increase in the yields of phenol and diphenyl ether. At a temperature higher than 150°C, chain reactions of phenol and diphenyl ether formation occurred. It is likely that the dissociation of halobenzene radical anions is the rate-limiting step of the processes.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Rossi, R.A. and de Rossi, R.H., Aromatic Substitution by the SRN1 Mechanism, Washington: American Chemical Society, 1983. Translated under the title Aromaticheskoe zameshchenie po mekhanizmu SRN1, Moscow: Mir, 1985.
Beletskaya, I.P. and Drozd, V.N., Usp. Khim., 1979, vol.45, no. 5, p. 793.
Mendkovich, A.S. and Gul'tyai, V.P., Teoreticheskie osnovy khimii organicheskikh anion-radikalov, (Fundamentals of Organic Radical Anion Chemistry), Moscow: Nauka, 1990.
Todres, Z.V., Ion-radikaly v organicheskom sinteze, (Radical Ions in Organic Synthesis), Moscow: Khimiya, 1986.
Yur'ev, Yu.K., Prakticheskie raboty po organicheskoi khimii, (Laboratory Works in Organic Chemistry), Moscow: Mosk. Gos. Univ., 1961.
Hart, E.J. and Anbar, M., The Hydrated Electron, New York: Wiley-Interscience, 1970. Translated under the title Gidratirovannyi elektron, Moscow: Atomizdat, 1973.
Dewar, M.J.S. and Thiel, W.J., J. Am. Chem. Soc., 1977, vol. 99, no. 15, p. 4899.
Pikaev, A.K., Sovremennaya radiatsionnaya khimiya. Radioliz gasov i zhidkostei, (Modern Radiation Chemistry: Radiolysis of Gases and Liquids), Moscow: Nauka, 1986.
Pikaev, A.K. and Kabakchi, S.A., Reaktsionnaya sposobnost' pervichnykh produktov radioliza vody. Spravochnik, (Reactivity of Primary Products of Water Radiolysis: A Handbook), Moscow: Energoizdat, 1982.
Stockdale, J.A., Hurst, G.S., and Christophorou, L.G., Nature (London), 1964, vol. 202, no. 3, p. 459.
Christophorou, L.G., Compton, R.N., Hurst, G.S., and Reinhardt, P.V., J. Chem. Phys., 1966, vol. 45, no. 2, p.536.
Wentworth, W., Becker, R., and Tung, R., J. Phys. Chem., 1967, vol. 71, no. 6, p. 1652.
Steelhammer, J.C. and Wentworth, W.E., J. Chem. Phys., 1969, vol. 51, no. 7, p. 1802.
Hiroshi, S., Takeyoshi, S., Yuji, O., and Yoshitsugu, T., Chem. Phys. Lett., 1995, vol. 232, nos. 1-2, p. 115.
Merg, G., Schuchmann, H.P., Madhava Rao, B.S., and von Sonntag, C., J. Chem. Soc., Perkin Trans. 2, 1996, no. 6, p. 1097.
Backlin, R. and Sherman, W.V., J. Chem. Soc., Chem. Commun., 1971, no. 9, p. 453.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kosobutskii, V.S. γ-Radiation-Initiated Formation of Phenol and Diphenyl Ether from Halobenzenes. High Energy Chemistry 37, 73–77 (2003). https://doi.org/10.1023/A:1022828214169
Issue Date:
DOI: https://doi.org/10.1023/A:1022828214169