Zinc (0)/dimethylformamide-mediated synthesis of symmetrical carboxylic anhydrides from acid chlorides

…, C Botuha, F Chemla, F Ferreira, A Pérez-Luna

Index: Serieys, Audrey; Botuha, Candice; Chemla, Fabrice; Ferreira, Franck; Perez-Luna, Alejandro Tetrahedron Letters, 2008 , vol. 49, # 36 p. 5322 - 5323

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Citation Number: 8

Abstract

The high yielding synthesis of symmetrical carboxylic anhydrides from acid chlorides mediated by zinc dust in the presence of dimethylformamide is presented. A mechanism involving the reductive insertion of zinc (0) into the C–Cl bond of a Vilsmeier-type iminium intermediate as the crucial step is also proposed.