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Amine- and ether-chelated aryllithium reagents-structure and dynamics.

Hans J Reich1, Wayne S Goldenberg, Aaron W Sanders

  • 1Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA. reich@chem.wisc.edu

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|March 20, 2003
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Chelation in phenyllithium reagents influences aggregation. Ether chelates compete with THF, while amine chelates show limited interaction, leading to significant dimer formation and specific structural insights.

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Area of Science:

  • Organometallic Chemistry
  • Organic Synthesis
  • Spectroscopy

Background:

  • Phenyllithium reagents are crucial in organic synthesis.
  • Understanding their aggregation state is key to controlling reactivity.
  • Chelation by ortho substituents can significantly alter reagent behavior.

Purpose of the Study:

  • To investigate the impact of chelating amine and ether substituents on phenyllithium aggregation.
  • To elucidate the structural consequences of chelation using advanced spectroscopic techniques.
  • To compare the chelating abilities of different ring sizes and heteroatoms (N vs. O).

Main Methods:

  • Variable temperature 6Li and 13C Nuclear Magnetic Resonance (NMR) spectroscopy.
  • 6Li and 15N isotope labeling studies.
  • Investigation of solvent additive effects, including Tetrahydrofuran (THF) and 1,1,4,7,10-pentamethyldiethylenetriamine (PMDTA).

Main Results:

  • 5- and 6-ring ether chelates (compounds 4, 5) effectively compete with THF.
  • 6-ring amine chelate (compound 2) shows weak competition, and 7-ring amine chelate (compound 3) shows no competition with THF.
  • Chelated phenyllithium reagents exhibit significantly enhanced dimerization compared to model compounds, with factors ranging from 40 to over 200,000.
  • A specific A-type dimer structure was assigned for 2-(2-dimethylaminoethyl)phenyllithium (2) via NMR coupling in isotopically labeled compounds.
  • Compound 2 monomer is not detectably chelated, while its dimer exhibits chelation.
  • 2-(methoxymethyl)phenyllithium (4) forms an open dimer and a pentacoordinate monomer.
  • Most lithium reagents form monomeric, non-chelated adducts with PMDTA.

Conclusions:

  • Chelation by ortho substituents strongly promotes dimerization in phenyllithium reagents.
  • Ether substituents are more effective chelators than amine substituents in competing with THF.
  • Specific structural assignments of chelated dimers are possible, providing insights into aggregation behavior.