Abstract
The bromination of 15 dinuclear phenolic compounds (dihydroxydiphenylmethanes, methylene bisphenols) by molecular bromine in acetic acid was studied kinetically at 22°C. In all compounds the electrophilic substitution occurred inortho-position to the phenolic hydroxy group of the methyl phenol unit while the non reacting neighboring unit was differently substituted by H, CH3,t-Bu and NO2. A decrease in the reaction rate was observed in 2,2′-dihydroxydiphenylmethanes, where the +M-effect of the hydroxy group is diminished by an intramolecular hydrogen bond. The strength of this hydrogen bond may be influenced mainly by steric factors. Strong electron withdrawing substituents like NO2 show a rate decreasing influence on the reactivity of the neighboring unit also in 2,4′- and 4,4′-dihydroxydiphenylmethanes.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literatur
Knop A., Scheib W., Chemistry and Application of Phenolic Resins. Berlin-Heidelberg-New York: Springer. 1979.
Böhmer V., Niemann W., Makromol. Chem.176, 2883 (1975).
Böhmer V., Niemann W., ibid.177, 787 (1976).
Cairns T., Eglinton G., Nature196, 535 (1962).
J. Chem. Soc.1965, 5906.
Kovac S., Solcaniova E., Baxa J., Tetrahedron27, 2283 (1971).
Sprengling G. R., J. Amer. Chem. Soc.76, 1190 (1954).
Böhmer V., Wamßer R., Kämmerer H., Monatsh. Chem.104, 1315 (1973).
Böhmer V., Deveaux J., Kämmerer H., Spectrochim. Acta28 A, 1977 (1972).
Z. B.Kämmerer H., Rausch W., Makromol. Chem.24, 152 (1957).
Böhmer V., Mathiasch B., Makromol. Chem.148, 41 (1971).
Böhmer V., Lotz W., Pachta J., Tütüncü S., Makromol. Chem.182, 2671 (1981).
Böhmer V., Wörsdörfer K., Becher U., Tetrahedron34, 2737 (1978).
Böhmer V.,Stein G., unveröffentlichte Versuche.
Kämmerer H., Happel G., Böhmer V., Org. Prep. Proced. Int.8, 245 (1976).
Wießler M., Diskussionsvortrag auf der 17. Hauptversammlung der GDCh in München (1977), Habilitationsschrift, Universität Heidelberg (1978).
Kanala A., Kovac S., Tetrahedron31, 2089 (1975).
Vgl. auchBöhmer V., Wamßer R., Kämmerer H., Monatsh. Chem.105, 501 (1974).
Niemann W., Böhmer V., Makromol. Chem.177, 803 (1976).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Böhmer, V., Stotz, D., Beismann, K. et al. Kinetik der Bromierung von Phenolen und phenolischen Mekrkernverbindungen. Monatsh Chem 114, 411–423 (1983). https://doi.org/10.1007/BF00798440
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00798440