Abstract
[591-51-5] C6H5Li (MW 84.05)
(organometallic agent useful as nucleophile for addition and substitution reactions,1, 3-20 and in the preparation of organolithium building blocks via metalation32 and lithium–metalloid exchange reaction1)
Physical Data: X-ray structures of the PMDTA-complexed monomer,2i the TMEDA-complexed dimer,2a the diethyl ether-complexed tetramer,2b and the PhLi∶LiBr (3∶1) mixed tetramer2b have been reported. Cryoscopic2h and NMR1 studies have shown that a monomer–dimer equilibrium exists in THF solution and that monomers exist in THF/HMPA2f and THF/PMDTA.2c PhLi is tetrameric in ether.
Solubility: sol ether solvents; sol hydrocarbon solvents only by the addition of donor solvents/additives such as ether or TMEDA.2a
Form Supplied in: commercially available in cyclohexane/ether solution.
Analysis of Reagent Purity: standard titration methods should be used.
Preparative Methods: prepared from phenyl halide (PhCl,2j PhBr,2k,l PhI2m) and lithium metal in ether. Several procedures have been used to prepare solid, salt-free PhLi.1 The synthesis of 13C-labeled PhLi (ipso carbon only) has been described.2h
Handling, Storage, and Precautions: moisture and oxygen sensitive. Concentrated solutions are pyrophoric. Ether solutions slowly undergo proton abstraction to generate benzene and should be stored in the freezer.
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