Chemical and physicochemical studies of homogeneous azidophenylselenylation of glycols with diacetoxyiodobenzene, trimethylsilyl azide, and diphenyl diselenide in dichloromethane revealed that the most probable key reaction step is the formation of phenylselenyl azide, an azide radical donor. A method for azidophenylsulfenylation of glycals was proposed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. F. G. Bongat, A. V. Demchenko, Carbohydr. Res., 2007, 342, 374.
R. A. Dwek, Chem. Rev., 1996, 96, 683.
H. Herzner, T. Reipen, M. Schultz, H. Kunz, Chem. Rev., 2000, 100, 4495.
R. Rai, I. McAlexander, C. W. T. Chang, Org. Prep. Proced. Int., 2005, 37, 337.
B. Casu, Adv. Carbohydr. Chem. Biochem., 1985, 43, 51.
J. Boullanger, D. Lafont, Chem. Rev., 1992, 92, 1167.
(a) R. U. Lemieux, R. M. Ratcliffe, Can. J. Chem., 1979, 57, 1244; (b) P. H. Seeberger, S. Rochrig, P. Schell, Y. Wang, W. J. Christ, Carbohydr. Res., 2000, 328, 61; (c) N. V. Bovin, S. E. Zurabyan, A. Ya. Khorlin, Carbohydr. Res., 1981, 98, 25; (d) A. Vassella, Ch. Witzig, J.-L. Chiara, M. Martin- Lomas, Helv. Chim. Acta, 1991, 74, 2073.
(a) G. Grundler, R. R. Schmidt, J. Lieb. Ann. Chem., 1984, 1826; (b) K. Briner, A. Vassella, Helv. Chim. Acta, 1987, 70, 1341; (c) A. Marra, F. Gauffeny, P. Sinay, Tetrahedron, 1991, 47, 5149; (d) J. B. Schwarz, S. D. Kuduk, X.-T. Chen, D. Sames, P. W. Glunz, S. J. Danishefsky, J. Am. Chem. Soc., 1999, 121, 2662.
(a) M. Tingoli, M. Tiecco, D. Chianelli, R. Balducci, A. Temperini, J. Org. Chem., 1991, 56, 6809; (b) M. Tingoli, M. Tiecco, L. Testaferri, A. Temperini, J. Chem. Soc., Chem. Commun., 1994, 1883; (c) S. Czernecki, E. Ayadi, D. Randriamandimby, J. Org. Chem., 1994, 59, 8256; (d) S. Czernecki, D. Randriamandimby, Tetrahedron Lett., 1993, 34, 7915; (e) F. Santoyo-Gonzales, F. G. Calvo-Flores, P. Garcia-Mendoza, F. Hernandez-Mateo, J. Isac-Garcia, R. Robles-Diaz, J. Org. Chem., 1993, 58, 6122.
Y. V. Mironov, A. A. Sherman, N. E. Nifantiev, Tetrahedron Lett., 2004, 9107.
Y. V. Mironov, A. A. Sherman, N. E. Nifantiev, Mendeleev Commun., 2008, 241.
(a) P. J. Stang, V. V. Zhdankin, Chem. Rev., 1996, 1123; (b) V. V. Zhdankin, P. J. Stang, Chem. Rev., 2002, 2523.
Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakurai, S. Oka, J. Am. Chem. Soc., 1994, 116, 3684.
W. G. Dauben, D. P. Bridon, B. A. Kowalczyk, J. Org. Chem., 1990, 55, 376.
M. Tingoli, A. Temperini, L. Testaferri, M. Tiecco, Angew. Chem., Int. Ed., 2003, 3131.
H. Duddeck, Progr. NMR Spectroscopy, 1995, 27, 1.
V. V. Zhdankin, C. J. Kuehl, A. P. Krasutsky, M. S. Formaneck, J. T. Bolz, Tetrahedron Lett., 1994, 35, 9677.
F. Minisci, Acc. Chem. Res., 1975, 165.
B. Kalyanaraman, E. G. Janzen, R. P. Mason, J. Biol. Chem., 1985, 260, 4003.
P. A. Evans, T. A. Brandt, J. Org. Chem., 1997, 62, 5321.
T. M. Klapotke, B. Krumm, K. Polborn, J. Am. Chem. Soc. 2004, 126, 710.
M. Tiecco, Top. Curr. Chem., 2000, 7.
S. Czernecki, E. Ayadi, D. Randriamandimby, J. Org. Chem., 1994, 59, 8256.
P. E. Cheshev, L. O. Kononov, Yu. E. Tsvetkov, A. S. Shashkov, N. E. Nifantiev, Bioorg. Khim., 2002, 28, 462 [Russ. J. Biorg. Chem. (Engl. Transl.), 2002, 28].
R. Weiss, J. Seubert, Angew. Chem., 1994, 900.
Author information
Authors and Affiliations
Corresponding author
Additional information
On the occasion of the 75th anniversary of the foundation of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 284–290, February, 2009.
Rights and permissions
About this article
Cite this article
Mironov, Y.V., Grachev, A.A., Lalov, A.V. et al. A study of the mechanism of the azidophenylselenylation of glycals. Russ Chem Bull 58, 284–290 (2009). https://doi.org/10.1007/s11172-010-0003-9
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-010-0003-9