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.
*Lecture presented at the 38th IUPAC Congress/World
Chemistry Congress 2001, Brisbane, Australia, 1-6 July 2001. Other presentations
are published in this issue, pp.1033-1145.
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