New developments in dimethyl carbonate chemistry

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...

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Veröffentlicht in:Pure and applied chemistry 2001-07, Vol.73 (7), p.1117-1124
1. Verfasser: Tundo, Pietro
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0033-4545
1365-3075
DOI:10.1351/pac200173071117