Abstract
The photolysis of ortho-azidophenol in water, ethanol, acetonitrile, chloroform, and benzene was studied by IR and electronic spectroscopy and thin-layer chromatography. It was found that an equilibrium between ortho-azidophenol and its quinonoid form occurred in benzene. In the photolysis of ortho-azidophenol in benzene, intramolecular hydrogen bonding facilitates the degradation of the azido group through the mechanism of formation of intermediate triazene structures. In the other solvents, which exclude intramolecular hydrogen bonding, the nitrene mechanism of photolysis yielding ortho-aminophenol, ortho-iminoquinone, and an azo compound is operative. The rate of formation of photolysis products depends on the nature of the solvent.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
The Chemistry of the Azido Group, Patai, S., Ed., London: Interscience, 1971, p. 626.
Karyakina, L.N. and Gubinov, A.V., Khim. Vys. Energ., 2000, vol. 34, no. 4, p. 300 [High Energy Chem., 2000, vol. 34, no. 4, p. 256].
Karyakina, L.N., Zhidkova, E.M., Yanin, A.M., and Oleinik, A.V., Khim. Vys. Energ., 1987, vol. 21, no. 4, p. 348.
Karyakina, L.N. and Oleinik, A.V., Khim. Vys. Energ., 1999, vol. 33, no. 3, p. 212 [High Energy Chem., 1999, vol. 33, no. 3, p. 179].
Karyakina, L.N., Korotina, T.B., and Oleinik, A.V., Khim. Vys. Energ., 1994, vol. 28, no. 4, p. 336 [High Energy Chem., 1994, vol. 28, no. 4, p. 294].
Karyakina, L.N., Kurenkova, G.V., Yanin, A.M., Babinkov, A.G., and Oleinik, A.V., Khim. Vys. Energ., 1989, vol. 23, no. 3, p. 263.
Karyakina, L.N., Novakovskaya, N.E., and Oleinik, A.V., Khim. Vys. Energ., 1994, vol. 28, no. 6, p. 516 [High Energy Chem., 1994, vol. 28, no. 6, p. 458].
Budruev, A.V., Karyakina, L.N, and Oleinik, A.V., Khim. Vys. Energ., 2003, vol. 37, no. 1, p. 33 [High Energy Chem., 2003, vol. 37, no. 1, p. 29].
Budruev, A.V., Karyakina, L.N., and Oleinik, A.V., Khim. Vys. Energ., 2004, vol. 38, no. 1, p. 24 [High Energy Chem., 2004, vol. 38, no. 1, p. 20].
Mazor, L., Methods of Organic Analysis, Budapest: Akademiai Kiado, 1983.
Bellamy, L.J, The Infra-Red Spectra of Complex Molecules, London: Methuen, 1954.
Nakanishi, K., Infrared Absorption Spectroscopy, San Francisco: Holden-Day, 1962.
Sheremet’ev, A.B., Usp. Khim., 1999, vol. 68, no. 2, p. 154.
Murata, Sh. and Tamioka, H., Chem. Lett., 1992, no. 1, p. 57.
Author information
Authors and Affiliations
Additional information
Original Russian Text © L.N. Karyakina, A.V. Oleinik, 2007, published in Khimiya Vysokikh Energii, 2007, Vol. 41, No. 2, pp. 142–146.
Rights and permissions
About this article
Cite this article
Karyakina, L.N., Oleinik, A.V. Photolysis of ortho-azidophenol in various solvents. High Energy Chem 41, 109–113 (2007). https://doi.org/10.1134/S0018143907020105
Received:
Issue Date:
DOI: https://doi.org/10.1134/S0018143907020105