Tetrahedron Letters

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

MD Wendt, AR Kunzer

Index: Wendt, Michael D.; Kunzer, Aaron R. Tetrahedron Letters, 2010 , vol. 51, # 4 p. 641 - 644

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Citation Number: 13

Abstract

A broad survey of aromatic compounds with halogens positioned both ortho and para to activating groups was studied in SNAr reactions with piperidine. Regioselectivities varied with the substituent group and the polarity of the solvent. Many activating groups exhibited an overall bias toward ortho-substitution, and this led in nonpolar solvents to very high ortho selectivity. More polar solvents uniformly shifted the product ratio toward para substitution. ...