Chemical Communications

Intramolecular aryl transfer to thionium ions in an approach to α-arylacetamides

C Ovens, JC Vogel, NG Martin…

Index: Ovens, Caroline; Vogel, Johannes C.; Martin, Nathaniel G.; Procter, David J. Chemical Communications, 2009 , # 21 p. 3101 - 3103

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Abstract

Here we describe a conceptually novel approach to α-arylacetamides that involves intramolecular aryl transfer to a thionium ion 4 generated in situ from a glyoxamide intermediate according to our reported procedure. 5 The synthetic sequence corresponds to the formal insertion of an acetic acid unit into the aryl and amine groups of an arylmethylamine that is dismantled during the key step (Scheme 1). The strategy involves the straightforward conversion of an ...