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Reaction of Dicarbonates with Carboxylic Acids Catalyzed by Weak Lewis Acids: General Method for the Synthesis of Anhydrides and Esters

Giuseppe Bartoli*, Marcella Bosco, Armando Carlone, Renato Dalpozzo, Enrico Marcantoni, Paolo Melchiorre, Letizia Sambri

*Dipartimento di Chimica Organica ‘A. Mangini', UniversitÓ di Bologna, Viale Risorgimento 4, 40136 Bologna, Italy, Email: bartolims.fci.unibo.it

G. Bartoli, M. Bosco, A. Carlone, R. Dalpozzo, E. Marcantoni, P. Melchiorre, L. Sambri, Synthesis, 2007, 3489-3496.

DOI: 10.1055/s-2007-990812


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Abstract

The reaction between carboxylic acids and dialkyl dicarbonates, in the presence of a weak Lewis acid such as magnesium chloride and the corresponding alcohol as the solvent, leads to esters in excellent yields. The mechanism involves a double addition of the acid to the dicarbonate, affording a carboxylic anhydride and CO2.

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proposed mechanism



Key Words

synthetic methods, anhydrides, esters, Lewis acids, magnesium salts


ID: J66-Y2007-3660