Ortho-selectivity in SN Ar substitutions of 2, 4-dihaloaromatic compounds. Reactions with anionic nucleophiles

MD Wendt, AR Kunzer

Index: Wendt, Michael D.; Kunzer, Aaron R. Tetrahedron Letters, 2010 , vol. 51, # 23 p. 3041 - 3044

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Citation Number: 8

Abstract

The nucleophilic addition of organic anions to aromatic compounds with halogens positioned both ortho and para to activating groups was studied in a variety of solvents. Substrates showed strong preferences for ortho substitution in most cases. Evidence is presented for activating group-dependent coordination, which contributes to very high ortho- selectivity in nonpolar solvents. This also drives the overall reaction rate in these solvents, ...