The dynamic covalent chemistry of mono- and bifunctional boroxoaromatics

Lyndsey M. Greig, Alexandra M.Z. Slawin, Melanja H. Smith, Douglas Philp*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

10-Hydroxy-10,9-boroxophenanthrene reacts rapidly and reversibly with both benzylic and alkane diols in non-polar solvents. The formation of 2:1 adducts between the boroxoaromatic and the diols is favoured. The diol component of the adduct can be exchanged readily and rapidly by treatment of the boroxoaromatic-diol adduct with an alternative diol in solution at room temperature. This reversible covalent chemistry would appear to be ideal for the dynamic assembly of more complex superstructures. However, attempts to extend this dynamic equilibrium to the assembly of macrocycles using the bifunctional boroxoaromatic 5,9-dihydroxy-5,9-dibora-4,10-dioxopyrene failed as a result of changes in the reactivity of the boron centre in the bifunctional boron-containing compound.

Original languageEnglish (US)
Pages (from-to)2391-2403
Number of pages13
JournalTetrahedron
Volume63
Issue number11
DOIs
StatePublished - Mar 12 2007

Keywords

  • Aromatic compounds
  • Dynamic covalent chemistry
  • Molecular recognition
  • Reversible reactions
  • Self-assembly

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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