Formation of Benzynes from 2,6-Dihaloaryllithiums: Mechanistic Basis of the Regioselectivity
Journal of the American Chemical Society2004Vol. 126(45), pp. 14700–14701
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Abstract
The key elimination step for the formation of 3-chloro- and 3-fluorobenzyne from 2-chloro-6-fluorophenyllithium displays a pronounced solvent-dependent regioselectivity. 6Li and 13C NMR spectroscopic studies on 2-chloro-6-fluorophenyllithium reveal a single monomeric aryllithium, suggested by DFT computational studies to be a trisolvate. Rate studies indicate that the elimination of LiCl and LiF proceeds via trisolvated and disolvated monomers, respectively.
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