Self-assembly in the metallation of bis(aminoaryl) ethers

Oldrich Kocian*, Neil Spencer, J. Fraser Stoddart, Ian Cragg-Hine, Matthew Davidson, Francis S. Mair, Paul Raithby, Ronald Snaith, Thomas Kottke, Ehmke Pohl

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

The dilithiation of 2,2′-bis(2-methoxyethylamino)diphenyl ether (4) and 2,2′-bis(N,N-dimethylethylenediamino)diphenyl ether (7) in the absence of any Lewis base donor resulted in the formation of dimeric complexes 8 and 9, respectively, containing the unprecedented Li4O2N4 "adamantanoid" metal core as a consequence of the self-recognition and self-assembly involving the two metallated subunits. In contrast, on monometallation using particular conditions, e.g. sodium hydride in the presence of Lewis base donor, the same ligands undergo a Smiles-type rearrangement, providing the first example of such a reaction involving an amine and a deactivated aromatic system. The conditions needed to promote this rearrangement have been investigated.

Original languageEnglish (US)
Pages (from-to)579-590
Number of pages12
JournalTetrahedron
Volume51
Issue number2
DOIs
StatePublished - Jan 9 1995

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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