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The Directed Lithiation of Benzenoid Aromatic Systems
Author(s) -
Wheatley Andrew E. H.
Publication year - 2003
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200300317
Subject(s) - chemistry , deprotonation , context (archaeology) , nuclear magnetic resonance spectroscopy , metal , crystal structure , single crystal , stereochemistry , ion , organic chemistry , crystallography , paleontology , biology
Directed metallation using organolithium bases is one of the best ways of regiospecifically elaborating aromatic systems and their substituents. For benzenoid arenes, deprotonation occurs at the ortho, lateral or peri positions. The reasons for each type of reaction will be considered in the context of the propensities of different directing groups for complex formation with the incoming organolithium base, acidification of the reactive site(s) and post‐reaction stabilisation of the metal ion(s). Discussion will concentrate on structural investigations, for the most part by single‐crystal X‐ray diffraction and/or by multinuclear NMR spectroscopy. Theoretical studies will also be incorporated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)