Abstract
Reactions of [fluoro(methylsulfonyloxy)iodo]benzene with norbornene, cis-5-norbornene-endo-2,3-dicarboxylic acid, and cis-5-norbornene-endo-2,3-dicarboxylic anhydride were studied. A new mild procedure was developed for introduction of fluoro and sulfonyloxy or two sulfonyloxy groups into molecules of norbornene and its derivatives.
Similar content being viewed by others
REFERENCES
Varvoglis, A., Synthesis, 1984, no. 9, pp. 709-726.
Pirkuliev, N.Sh., Brel', V.K., and Zefirov, N.S., Usp. Khim., 2000, vol. 69, no. 2, pp. 118-133.
Kasumov, T.M., Pirguliyev, N.Sh., Brel, V.K., Grishin, Y.K., Zefirov, N.S., and Stang, P.J., Tetrahedron, 1997, vol. 53, no. 38, pp. 13139-13148.
Pirkuliev, N.Sh., Brel', V.K., Kasumov, T.M., Akhmedov, N.G., Zefirov, N.S., and Stang, P.J., Russ. J. Org. Chem., 1999, vol.35, no. 11, pp. 1600-1603.
Pirguliyev, N.Sh., Brel, V.K., Kasumov, T.M., Grishin, Y.K., Zefirov, N.S., and Stang, P.J., Synthesis, 1999, no. 8, pp. 1297-1299.
Pirguliyev, N.Sh., Brel, V.K., Zefirov, N.S., and Stang, P.J., Mendeleev Commun., 1999, no. 5, pp. 189-190.
Pirkuliev, N.Sh., Brel', V.K., and Zefirov, N.S., Abstracts of Papers, Mezhdunarodnaya nauchnaya konferentsiya “Organicheskii sintez i kombinatornaya khimiya” (Int. Scientific Conf. “Organic Synthesis and Combinatorial Chemistry”), Moscow, 1999, P-131.
Pirkuliev, N.Sh., Brel', V.K., Akhmedov, N.G., and Zefirov, N.S., Russ. J. Org. Chem., 2000, vol. 36, no. 9, pp. 1282-1287.
Pirkuliev, N.Sh., Brel', V.K., Akhmedov, N.G., Magerramov, A.M., Shikhaliev, N.G., and Zefirov, N.S., Russ. J. Org. Chem., 2001, vol. 37, no. 5, pp. 683-686.
Kwart, H. and Kaplan, L., J. Am. Chem. Soc., 1954, vol. 76, no. 16, pp. 4072-4077.
Roberts, J.D., Johnson, F.O., and Carboni, R.A., J. Am. Chem. Soc., 1954, vol. 76, no. 22, pp. 5692-5699.
Rebrovic, L. and Koser, G.F., J. Org. Chem., 1984, vol. 49, no. 13, pp. 2462-2472.
Zefirov, N.S., Zhdankin, V.V., Dan'kov, Yu.V., Semerikov, V.N., Chizhov, O.S., and Koz'min, A.S., Dokl. Akad. Nauk SSSR, 1986, vol. 288, no. 2, pp. 385-388.
Grutzner, J.V., Jautelat, M., Dence, J.B., Smith, J.A., and Roberts, J.D., J. Am. Chem. Soc., 1970, vol. 92, no. 24, pp. 7107-7120.
Stepanyants, A.U., Bystrov, V.F., and Kagramanyan, A.V., Zh. Strukt. Khim., 1971, vol. 12, no. 2, pp. 224-230.
Marchand, A.P. and Rose, J.E., J. Am. Chem. Soc., 1968, vol. 90, no. 14, pp. 3724-3731.
Zefirov, N.S., Sadovaya, N.K., Novgorodtseva, L.A., and Bodrikov, I.V., Tetrahedron, 1978, vol. 34, no. 9, pp. 1373-1376.
Brown, H.C., Kawakami, J.H., and Kwang-Ting Liu, J. Am. Chem. Soc., 1973, vol. 95, no. 7, pp. 2209-2216.
Koz'min, A.S., Doctoral (Chem.) Dissertation, Moscow, 1983.
Kato, M., Kageyama, M., and Tanaka, R., J. Org. Chem., 1975, vol. 40, no. 13, pp. 1932-1941.
Bellamy, L.J., The Infra-red Spectra of Complex Molecules, London: Methuen, 1958. Translated under the title Infrakrasnye spektry slozhnykh molekul, Moscow: Inostrannaya Literatura, 1963, pp. 256-275.
Perrin, D.D., Armarego, W.L.F., and Perrin, D.R., Purification of Laboratory Chemicals, Oxford: Pergamon, 1980, pp. 79-81, 205.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Pirkuliev, N.S., Brel, V.K., Akhmedov, N.G. et al. Reactions of [Fluoro(methylsulfonyloxy)iodo]benzene: III. Reactions of [Fluoro(methylsulfonyloxy)iodo]benzene with Norbornene and Some Its Derivatives. Russian Journal of Organic Chemistry 37, 1001–1007 (2001). https://doi.org/10.1023/A:1012482617980
Issue Date:
DOI: https://doi.org/10.1023/A:1012482617980