Regioselective Nucleophilic Aromatic Substitution: Unexpected Results in the Thiophene Series

Evelyne Migianu; Damien Prim; Gilbert Kirsch

doi:10.1055/s-2000-6560

Synlett 2000; 2000(4): 459-462
DOI: 10.1055/s-2000-6560

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Regioselective Nucleophilic Aromatic Substitution: Unexpected Results in the Thiophene Series

Evelyne Migianu^* , Damien Prim, Gilbert Kirsch

^*Groupe de Synthèse Organique et Hétérocyclique, Laboratoire de Chimie Organique, Université de Metz, Ile du Saulcy, F-57045 Metz Cedex, France; E-mail: prim@sciences.univ-metz.fr

Abstract

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The present study points out the unconventional behaviour of thiophene ring bearing two leaving groups and a weak electron withdrawing moiety towards nucleophilic attack. The S_NAr using secondary amines shows an unexpected regioselectivity: the para-like adduct is produced as the major isomer for the first time. The influence of several reaction conditions on the selectivity observed is investigated.

aminothiophene - nucleophilic aromatic substitution - regioselectivity

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