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Dimethylcarbonate as a Green Reagent

  • Pietro Tundo
    Pietro Tundo
    Department of Environmental Science, Cà Foscari University, Dorsoduro 2137, Venice 30123, Italy
    More by Pietro Tundo
  • Maurizio Selva
    Maurizio Selva
    Department of Environmental Science, Cà Foscari University, Dorsoduro 2137, Venice 30123, Italy
  • , and 
  • Sofia Memoli
    Sofia Memoli
    Interuniversity Consortium "Chemistry for the Environment", Via della Libertá 5/12, 30175 Marghera, Venice, Italy
    More by Sofia Memoli
DOI: 10.1021/bk-2000-0767.ch008
Publication Date (Print):August 15, 2000
Green Chemical Syntheses and Processes
Chapter 8pp 87-99
ACS Symposium SeriesVol. 767
ISBN13: 9780841236783eISBN: 9780841218208
Copyright © 2000 American Chemical Society
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Abstract

Dimethylcarbonate (DMC) is an environmentally friendly substitute for dimethylsulfate (DMS) and methyl halides in methylation reactions. It is also a very selective reagent. The reactions of DMC with methylene-active compounds produce monomethylated derivatives with a selectivity not previously observed. The batchwise monomethylation of arylacetonitriles, arylacetoesters, aroxyacetonitriles, methyl aroxyacetates, benzylarylsulfones and alkylarylsulfones with DMC achieve >99% selectivity at 180-220°C in the presence of K2CO3. Mono-N-methylation of primary aromatic amines at 120-150 °C in the presence of Y- and X-type zeolites, achieved selectivities up to 97%. At high temperature (200°C) and in the presence of potassium carbonate as the catalyst, DMC splits benzylic and aliphatic ketones into two methyl esters; in contrast, DMC converts ketone oximes bearing a methylene group to 3-methyl-4,5-disubstituted-4-oxazolin-2-ones. Dibenzylcarbonate (DBzlC) exhibits similar reactivity, selectively monobenzylating methylene-active compounds.

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