Selective monomethylation reactions of methylene-active compounds
with dimethylcarbonate. An example of clean synthesis*
Pietro Tundo
Department of Environmental Science, Cà Foscari
University of Venice and Interuniversity Consortium "Chemistry
for the Environment", Italy
Abstract: Dimethylcarbonate (DMC), an environmentally friendly
substitute for dimethylsulfate and methyl halides in methylation reactions,
is also a very selective reagent. Under batch conditions, with potassium
carbonate as the catalyst, the reactions of DMC, used as the solvent
of the reactions, with methylene-active compounds (arylacetonitriles
and arylacetoesters, aroxyacetonitriles and methyl aroxyacetates, benzylaryl-
and alkylaryl-sulfones) produce monomethylated derivatives, with a selectivity
not previously observed (i. e., >99%). These are examples of "green
chemistry".
*Lecture presented at the 13th International
Conference on Organic Synthesis (ICOS-13), Warsaw, Poland, 1-5 July
2000.
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