Unusual structures of lithium terphenyl derivatives

Ned J. Hardman, Brendan Twamley, Matthias Stender, Richard Baldwin, Shirley Hino, Berthold Schiemenz, Susan M. Kauzlarich, Philip P. Power

Research output: Contribution to journalArticle

33 Scopus citations

Abstract

The synthesis, spectroscopic and structural characterization of three new lithium derivatives of terphenyl ligands are reported. These are the mixed lithium alkyl-lithium aryl compound {Li(t-Bu)LiC6H3-2,6-Trip2} (1, Trip = C6H2-2,4,6-i-Pr3), the dilithiated The synthesis of the terphenyl halide precursors for 2 and 3 is also given. The compound 1 resulted from the treatment of 1-IC6H3-2,6-Trip with two equivalents of Li(t-Bu) in hexane. It features the alkyl and aryl (terphenyl) groups bridged by two lithium ions. The lithium ions are further solvated by ortho aryl substituents and methyls of the t-Bu groups. This compound is a very rare example of a mixed lithium alkyl-lithium aryl species. Compound 2 was obtained in low yield from the treatment of 1-BrC6H3-2,6-(C6H 3-2-Me-5-t-Bu)2 with two equivalents of Li(t-Bu). The terphenyl ligand was dilithiated by replacement of the bromine and a hydrogen from one of the methyl groups on the ortho aryl substituents. The ether solvated, dimeric, tetrametallic structure illustrated in the Table of Contents resulted. The compound 3 was obtained from the straightforward lithiation of the iodoterphenyl precursor in the presence of diethyl ether and features a lithium ion solvated by two ethers terminally bound to the ipso-carbon of the terphenyl group.

Original languageEnglish (US)
Pages (from-to)461-467
Number of pages7
JournalJournal of Organometalic Chemistry
Volume643-644
DOIs
StatePublished - Feb 1 2002

Keywords

  • Bulky groups
  • C-H activation
  • Lithium alkyl
  • Lithium aryl
  • Terphenyl

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

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    Hardman, N. J., Twamley, B., Stender, M., Baldwin, R., Hino, S., Schiemenz, B., Kauzlarich, S. M., & Power, P. P. (2002). Unusual structures of lithium terphenyl derivatives. Journal of Organometalic Chemistry, 643-644, 461-467. https://doi.org/10.1016/S0022-328X(01)01443-7