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Synergic synthesis of benzannulated zincabicyclic complexes, alpha-zincated n ylides, through sodium-TMEDA-mediated zincation of a haloarene

Armstrong, D.R. and Balloch, L. and Clegg, William and Dale, S.H. and Garcia-Alvarez, P. and Hevia, E. and Hogg, L.M. and Kennedy, A.R. and Mulvey, R.E. and O'Hara, Charles (2009) Synergic synthesis of benzannulated zincabicyclic complexes, alpha-zincated n ylides, through sodium-TMEDA-mediated zincation of a haloarene. Angewandte Chemie, 48 (46). pp. 8675-8678. ISSN 0044-8249

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Abstract

Double role for sodium: Within a synergic sodium TMP-zincate reagent, sodium mediates the direct ortho-zincation of chlorobenzene and delivers the TMEDA ligand to nucleophilically attack the benzene ring, thereby generating novel open and cyclic zinc zwitterions (example shown). TMP=2,2,6,6-tetramethylpiperidide; TMEDA=N,N,N,N-tetramethylethylenediamine.