Abstract
Reactions of N-substituted bicyclo[2.2.1]hept-5-ene-endo-2,endo-3-dicarboximides with o- and p-nitrophenyl azides, as well as with p-nitrophenylsulfonyl azide and p-toluenesulfonyl azide, afforded the corresponding substituted dihydrotriazole (from aryl azides) and arylsulfonylaziridine derivatives (from sulfonyl azides). The exo orientation of the nitrogen-containing cyclic fragments (in keeping with the Alder rule) and endo orientation of the imide ring were confirmed by analysis of the IR and 1H and 13C NMR spectra. The molecular structure of one of the products was examined by X-ray analysis.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Onishchenko, A.S., Dienovyi synthesis(Diels-Alder Reaction), Moscow: Akad. Nauk SSSR, 1963; Zefirov, N.S. and Sokolov, V.I., Usp. Khim. 1967, vol. 36, p. 243.
L'abbe, G., Chem. Rev., 1969, vol. 69, p. 345; Scriven, E.F.V. and Turnbull, K., Chem. Rev., 1988, vol. 88, p. 297.
Shea, K.J. and Kim, J., J. Am. Chem. Soc., 1992, vol. 114, p. 4846.
Scheiner, P., Schomaker, J.H., and Deming, S., J. Am. Chem. Soc., 1965, vol. 87, p. 306; Samuilov, Ya.D., Movchan, A.I., and Konoshenko, L.V., Zh. Org. Khim., 1981, vol. 17, p. 1626; Roof, A.A.M., Winter, W.J., and Bartlett, P.D., J. Org. Chem., 1985, vol. 50, p. 4093.
Scheiner, P. and Vaughan, W.R., J. Org. Chem., 1961, vol. 26, p. 1923.
Zalkow, L.H. and Oehlschlager, A.C., J. Org. Chem., 1963, vol. 28, p. 3303; Zalkow, L.H. and Ken-nedy, C.D., J. Org. Chem., 1963, vol. 28, p. 3309; Oehlschlager, A.C. and Zalkow, L.H., Can. J. Chem., 1969, vol. 47, p. 461.
Gassmann, P.G., Schaffhausen, J.G., Starkey, F.D., and Raynolds, P.W., J. Am. Chem. Soc., 1982, vol. 104, p. 6411.
Kas'yan, L.I., Usp. Khim., 1998, vol. 67, p. 299; Kas'yan, L.I., Seferova, M.F., and Okovityi, S.I., Alitsiklicheskie epoksidnye soedineniya. Metody sinteza(Alicyclic Epoxy Compounds. Methods of Synthesis), Dnepropetrovsk: Dnepropetr. Gos. Univ., 1996.
Kas'yan, L.I., Krishchik, O.V., Umrikhina, L.K., and Kas'yan, A.O., Visn. Dnipropetr. Univ., Khim., 1998, vol. 3, p. 87; Moench, S.I., Pagani, G., Gaecialanza, G., Viearini, L., and Baruffini, A., Farmaco, Ed. Sci., 1970, vol. 25, p. 203.
Nakanishi, K., Infrared Absorption Spectroscopy. Practical, San Francisco: Holden-Day, 1962.
Bellamy, L.J., The Infra-red Spectra of Complex Molecules, London: Methuen, 1958.
Burgi, H.-B. and Dunitz, G.D., Structure Correlation, Weinheim: VCH, 1994, vol. 2, p. 741.
Zefirov, Yu.V. and Zorkii, P.M., Usp. Khim., 1989, vol. 58, p. 713.
Organic Syntheses, Noland, W.E., Ed., New York: Wiley, 1963, collect. vol. 4; Organic Syntheses, Baum-garten, H.E., Ed., New York: Wiley, 1973, collect. vol. 5.
Tori, K., Aono, K., Kitahonoki, K., Muneyuki, R., Takano, Y., Tanida, H., and Tsuji, T., Tetrahedron Lett., 1966, p. 2921; Zefirov, N.S., Kasyan, L.I., Gneden-kov, L.Yu., Shashkov, A.S., and Cherepanova, H.G., Tetrahedron Lett., 1979, p. 949; Shashkov, A.S., Chere-panova, E.G., Kas'yan, L.I., Gnedenkov, L.Yu., and Bombushkar', M.F., Izv. Akad. Nauk SSSr, Ser. Khim., 1980, p. 564.
Sheldrick, G.M., SHELX97. PC Version. A System of Computer Programs for the Crystal Structure Solution and Refinement, 1998. Rev. 2.
Rights and permissions
About this article
Cite this article
Tarabara, I.N., Kas'yan, A.O., Yarovoi, M.Y. et al. Reactions of Bicyclo[2.2.1]hept-5-ene-2,3-dicarboximides with Aromatic Azides. Russian Journal of Organic Chemistry 40, 992–998 (2004). https://doi.org/10.1023/B:RUJO.0000045191.12939.47
Issue Date:
DOI: https://doi.org/10.1023/B:RUJO.0000045191.12939.47