Calixhydroquinones: A novel access to conformationally restricted, meta-substituted calixarenes

Mark Mascal, Ralf Warmuth, Russell T. Naven, Ross A. Edwards, Michael B. Hursthouse, David E. Hibbs

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Abstract

An efficient and versatile synthetic route to calixhydroquinones is described. These macrocycles are activated towards meta substitution, and reaction with bromine gives the first examples of persubstituted, phenol-derived calixarenes. The effect of meta substitution on calixarene mobility is demonstrated by the fixation of an otherwise mobile calix[4] system in the partial cone conformer, and the slowing of the ring inversion rate in calix[8]arenes.

Original languageEnglish (US)
Pages (from-to)3435-3441
Number of pages7
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number23
DOIs
Publication statusPublished - Dec 7 1999
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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