Abstract
4-Dibromomethyl-4-methyl-2,5-cyclohexadienone and its 2- and 3-methyl-substituted derivatives react with an equimolar amount of molecular bromine in carbon tetrachloride, yielding vinyl bromination products at the α-position with respect to the carbonyl group. The reaction of 4-dibromomethyl-3,4-dimethyl-2,5-cyclohexadienone with a large excess of bromine, apart from the vinyl bromination product, gives the corresponding 3-bromomethyl and 3-dibromomethyl derivatives. 4-Dibromomethyl-2,4-dimethyl-2,5-cyclohexadienone takes up bromine molecule at the C2ÍC3 double bond.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Auvers, K. and Keil, G., Ber., 1902, vol. 35, p. 4207.
Fieser, L.F. and Fieser, M., Advanced Organic Chemistry, New York: Reinhold, 1962. Translated under the title Organicheskaya khimiya, Moscow: Mir, 1966, vol. 2, p. 391.
Ravina, E., Montanes, I.M., Silyro, M.P., and Tato, F., Ann. Quim., 1973, vol. 69, p. 915; Chem. Abstr., 1974, vol. 80, no. 14 610 n.
Ravina, E., Montanes, I.M., Cobreros, M.T., and Tato, F., Chim. Ther., 1973, vol. 8, p. 290.
Nikanorov, V.A., Gavrilova, G.V., Sergeev, S.V., Rozenberg, V.I., and Reutov, O.A., Metalloorg. Khim., 1989, vol. 2, p. 102.
Gavrilova, G.V., Krut'ko, D.P., Gavrilov, A.A., and Butin, K.P., Izv. Ross. Akad. Nauk, Ser. Khim., 1997, p. 1642.
Gavrilova, G.V., Krut'ko, D.P., Gavrilov, A.A., and Butin, K.P., Izv. Ross. Akad. Nauk, Ser. Khim., 1997, p. 1015.
Friedrich, E.G., J. Org. Chem., 1968, vol. 33, p. 413.
Woodward, R.B., J. Am. Chem. Soc., 1940, vol. 62, p. 1208.
Auvers, K. and Ziegler, K., Justus Liebigs Ann. Chem., 1921, vol. 425, pp. 301, 304, 306, 309.
Perry, N.B., Blunt, J.W., and Munro, M.H.G., Tetrahedron, 1988, vol. 44, p. 1727.
Munro, M.N.G., Blunt, J.W., Barns, G., Battershill, C.N., Lake, R.J., and Perry, N.B., Pure Appl. Chem., 1989, vol. 61, p. 529.
Minale, L., Cimino, G., De Stefano, S., and Sodano, G., Fortschr. Chem. Org. Naturst., 1976, vol. 33, p. 1.
Thompson, J.E., Walker, R.P., and Faulkner, D.J., Marine Biol., 1985, vol. 83, p. 11.
Morton, I.D. and Robertson, P.W., J. Chem. Soc., 1945, p. 129.
March, J., Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, New York: Wiley, 1985. Translated under the title Organicheskaya khimiya, Moscow: Mir, 1987, vol. 3, p. 76.
Dauben, H.J. and McCoy, L.L., J. Am. Chem. Soc., 1959, vol. 81, p. 4853.
Barbier, M., Barton, D.H.R., Devys, M., and Topgi, R.S., Tetrahedron, 1987, vol. 43, p. 5031.
Merchant, J.R. and Desai, V.B., J. Chem. Soc., 1968, p. 499.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Gavrilova, G.V., Gavrilov, A.A., Krut'ko, D.P. et al. Reaction of Some Dibromomethyl-Substituted Cyclohexadienones with Molecular Bromine. Russian Journal of Organic Chemistry 39, 361–367 (2003). https://doi.org/10.1023/A:1025589614195
Issue Date:
DOI: https://doi.org/10.1023/A:1025589614195