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Pure Appl. Chem., 2001, Vol. 73, No. 7, pp. 1117-1124

New developments in dimethyl carbonate chemistry

Pietro Tundo

Dipartimento di Scienze Ambientali, Università Ca' Foscari Dorsoduro 2137 ­ 30123 Venezia, Italy

Abstract: Dimethylcarbonate (DMC) is a valuable methylating reagent which can replace methyl halides and dimethylsulfate in the methylation of a variety of nucleophiles. It couples tunable reactivity and unprecedented selectivity toward mono-C- and mono-N-methylation in the reactions of acidic CH2 and primary aromatic amines, respectively. In addition, it is a prototype example of a green reagent, since it is nontoxic, made by a clean process, and biodegradable, and it reacts in the presence of a catalytic amount of base thereby avoiding the formation of undesirable inorganic salts as by-products. Other remarkable reactions are those where DMC behaves as an oxidant: cyclic ketones are transformed into a,w-dimethyl esters with a reaction of atom efficiency of 1.0.