Journal
PURE AND APPLIED CHEMISTRY
Volume 73, Issue 7, Pages 1117-1124Publisher
INT UNION PURE APPLIED CHEMISTRY
DOI: 10.1351/pac200173071117
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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 alpha,omega -dimethyl esters with a reaction of atom efficiency of 1.0.
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