Green organic syntheses: organic carbonates as methylating agents.
Dimethylcarbonate (DMC) is a valuable methylating reagent that can replace methyl halides and dimethylsulfate in the methylation of a variety of nucleophiles. It couples tunable reactivity and unprecedented selectivity towards mono-C- and mono-N-methylation. In addition, it is a prototype example of a green reagent, because it is nontoxic, is made by a clean process, is biodegradable, and reacts in the presence of a catalytic amount of base, thereby avoiding the formation of undesirable inorganic salts as by-products. Depending on the reaction conditions, DMC can be reacted under plug-flow, CSTR, or batch conditions. Other remarkable reactions are those where DMC behaves as an oxidant. The reactivity of other carbonates is reported as well.
Tundo
Pietro
P
Dipartimento di Scienze Ambientali, Università Ca' Foscari, Dorsoduro 2137-30123, Venezia, Italy. tundop@unive.it
Perosa
Alvise
A
D000477:Alkylating Agents / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry*; D007220:Industrial Waste / Q000517:prevention & control*; D008745:Methylation; D009930:Organic Chemicals / Q000138:chemical synthesis*
D000477:Alkylating Agents; D002254:Carbonates; D007220:Industrial Waste; D009930:Organic Chemicals