Monatshefte für Chemie / Chemical Monthly

, Volume 114, Issue 4, pp 411–423 | Cite as

Kinetik der Bromierung von Phenolen und phenolischen Mekrkernverbindungen

4. Der Einfluß des Nachbarbausteins auf die Reaktivität von Dihydroxydiphenylmethanen
  • Volker Böhmer
  • Diethard Stotz
  • Klaus Beismann
  • Wilhelm Niemann
Organische Chemie Und Biochemie
Received:
Accepted:

Kinetics of the bromination of phenols and oligonuclear phenolic compounds, 4. The influence of the neighboring phenolic unit on the reactivity of dihydroxydiphenylmethanes

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.

Keywords

Bromination Dihydroxydiphenylmethanes Intramolecular hydrogen bonding Kinetics 
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Copyright information

© Springer-Verlag 1983

Authors and Affiliations

  • Volker Böhmer
    • 1
  • Diethard Stotz
    • 1
  • Klaus Beismann
    • 1
  • Wilhelm Niemann
    • 1
  1. 1.Organisch-chemisches InstitutUniversität MainzMainzBundesrepublik Deutschland

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