Formation of benzynes from 2,6-dihaloaryllithiums: mechanistic basis of the regioselectivity.

نویسندگان

  • Antonio Ramírez
  • John Candler
  • Crystal G Bashore
  • Michael C Wirtz
  • Jotham W Coe
  • David B Collum
چکیده

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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عنوان ژورنال:
  • Journal of the American Chemical Society

دوره 126 45  شماره 

صفحات  -

تاریخ انتشار 2004