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Controlling Chemoselectivity in the Lithiation of Substituted Aromatic Tertiary Amides

Angewandte Chemie, 2004
Solvent effects control the regioselectivity with which tert-butyllithium deprotonates 2-ethyl-N,N-diisopropyl-1-benzamide. From THF an ortho-lithiated dimer is isolated but from N,N,N′,N″, N″pentamethyldiethylenetriamine (pmdeta) a laterally lithiated monomer is obtained (see scheme).
Armstrong, David R.   +7 more
openaire   +4 more sources

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