Reaction of Sodium Azide with 1,1'–Dicyclohexenyl–Diepoxides

Document Type : Research Article


1 Department of Chemistry, Faculty of Science, University of Tehran, Tehran, I.R. IRAN

2 Research Institute of Petroleum Industry, National Iranian Oil Company, Tehran, I.R. IRAN



Nucleophilic ring opening of dl and meso 1,1¢- dicyclohexenyl diepoxides by sodium azide in dioxane and aqueous alcoholic medium give the corresponding azidoalcohols. The obtention of departure diepoxides from diazidoalcohols by the reaction with sodium hydride shows the anti position of OH and N3 groups.


Main Subjects

[1] a) Ross., W.C., J. Chem. Soc., 2257 (1950).
b) Kupchan, S. M., Memengway, R. J. and Smith., R. M., J. Org. Chem., 34, 3898 (1969).
c) Schvlte, K. H., Gadola, M. and Ohloff. G., Chem. Acta., 50, 2028 (1973).
d) Borders, D. B., Barbatschi, F., and Shag. A. J., Antimicrob. Age. Chemother., 223 (1970).
e) Ogawa, S., Oki, S., and Suami., T., Bull . Chem. Soc. of Jpn., 53, 2895 (1980).
[2] Razenko, Z. W., Mukhov, A.N., Kornev., A.K., Chem. abs. 72, 67541g (1970).
[3] a) Vince, R. and Daluge, S., J. Med. Chem., 17 (6) 578 (1974).
b) Mitrochkine, A., Gil, G. and Reglier. M., Tetrahedron asymmetry., 617, 1535 (1995).
[4] Darvich,  M. R., and  Abdoh, Y.,  Q. Bull.  Fac. Sci, Tehran. Univ., 10(1) (1978), 1 and references cited therein (C.A, 92, 21717 j, 1980).
[5] Hanessian, S., and Wang, J., Can. J.Chem., 71(12) 2102 (1993).
[6] Enikolopiyan, N.S., Pure and Appl. chem., 48, 317(1976).
[7] Tobe, Y., Iketani, H., Tsuchia, Y., Konishi, M., and Nalmura, K., Tetrahedron asymmetry, 8, 3735 (1997).
[8] Berti, G., Macchia, B., and Macchia, F., Tetrah-edron.,  24, 1755 (1968).
[9] Plenat, F., Pietrasanta, F.,  Darvich, M. R., and Christol. H., Bull. Soc. Chim. Fr., 1-2, 361 (1975).
[10] Vilkas, M., Bull. Soc. Chim. Fr., 1401 (1959).