Molecular catalysis by quaternary ammonium salts: cyclisation of 2-(3-halopropyl)-4-nitrophenols

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The cyclisation of 2-(3-halopropyl)-4-nitrophenols 4-6 is an intramolecular nucleophilic substitution with clean first-order kinetics. The rate is influenced by the macrotricyclic ammonium salt 2 by virtue of a 1:1 hostguest complex formation. Inhibition is observed with the chloro compound 4 and to a minor extent with the bromo analog 5, whereas a moderate rate acceleration was found with iodo compound 6. Inspection of the temperature dependence of the rate effects leads to the conclusion that 2 may be regarded as a dipolar aprotic microsolvent.

Original languageEnglish
Pages (from-to)141-149
Number of pages9
JournalJournal of Molecular Catalysis
Issue number2-3
StatePublished - Oct 1986


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