Abstract
Reactions of (1R,4R)-7,7-dimethyl-1-vinylnorbornan-2-one with bromine in carbon tetrachloride and with N-bromosuccinimide in methanol gave the corresponding C1 '-epimeric dibromo and methoxy bromo derivatives. Their structure was determined on the basis of spectral data.
Similar content being viewed by others
REFERENCES
Money, T., Nat. Prod. Rep., 1985, vol. 2, no. 2, pp. 253-288.
Clase, J.A. and Money, T., Can. J. Chem., 1992, vol. 7, no. 26, pp. 1537-1544.
Hutchinson, J.H., Money, T., and Piper, S.E., Can. J. Chem., 1986, vol. 64, no. 13, pp. 854-860.
Hutchinson, J.H. and Money, T., Tetrahedron Lett., 1985, vol. 26, no. 15, pp. 1819-1822.
Stevens, R.V. and Lawrence, D.S., Tetrahedron, 1985, vol. 41, no. 1, pp. 93-100.
Stevens, R.V., Gaeta, F.C.A., and Lawrence, D.S., J. Am. Chem. Soc., 1983, vol. 105, no. 26, pp. 7713-7719.
Stevens, R.V., Chang, J.M., Lapalme, R., Schow, S., Schaltager, M.G., Shapiro, R., and Weller, H.N., J. Am. Chem. Soc., 1983, vol. 105, no. 26, pp. 7719-7729.
Vaillancourt, V., Agharahimi, M.R., Sundran, U.N., Richou, O., Faulkner, D.J., and Albizati, K., J. Org. Chem., 1991, vol. 56, no. 1, pp. 378-387.
Fischer, N. and Opitz, G., Organic Synthesis, New York: Wiley, 1973, p. 877.
Dixon, A.J., Taylor, R.J.K., Newton, R.F., Wadsworth, A.H., and Klinkert, G., J. Chem. Soc. Perkin Trans. 1, 1982, no. 5, pp. 1923-1932.
Rodrigues, J. and Dulcere, J.-P., Synthesis, 1993, no. 3, p. 1177.
Davis, F.A., Lamendola, J., Nadir, U., Kluger, E.W., Sedergan, T.C., Panuuto, T.W., Billmers, R., Jenkins, R., Turchi, I.J., Watson, W.H., Chen, J.S., and Kimura, M., J. Am. Chem. Soc., 1980, vol. 102, no. 6, pp. 2000-2005.
Kaye, P.T. and Molema, W.E., Synth. Commun., 1999, vol. 29, no. 11, pp. 1889-1902.
Kiegel, K., Prokopowich, P., and Jurczak, J., Synth. Commun., 1999, vol. 29, no. 22, pp. 3999-4005.
Mizijiri, R., Urabe, H., and Sato, F., Angew. Chem., Int. Ed. Engl., 1998, vol. 110, no. 19, pp. 2666-2668.
Vostrikov, N.S., Abutkov, A.V., and Miftakhov, M.S., Russ. J. Org. Chem., 2001, vol. 37, no. 8, pp. 1102-1106.
Wang, Z.-M. and Shon, M., J. Org. Chem., 1998, vol. 63, no. 5, pp. 1414-1418.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Vostrikov, N.S., Abutkov, A.V., Vasikov, V.Z. et al. Vicinal Dibromo and Hydroxy(methoxy) Bromo Derivatives of (1R,4R)-7,7-Dimethyl-1-vinylnorbornan-2-one. Regio- and Stereoselectivity Aspects. Russian Journal of Organic Chemistry 38, 658–661 (2002). https://doi.org/10.1023/A:1019602804144
Issue Date:
DOI: https://doi.org/10.1023/A:1019602804144