dc.creatorTundo, Pietro
dc.creatorBressanello, Salimo
dc.creatorLoris, Alessandro
dc.creatorSathicq, Angel Gabriel
dc.date.accessioned2018-08-14T14:10:28Z
dc.date.available2018-08-14T14:10:28Z
dc.date.created2018-08-14T14:10:28Z
dc.date.issued2005-10
dc.identifierTundo, Pietro; Bressanello, Salimo; Loris, Alessandro; Sathicq, Angel Gabriel; Direct synthesis of N-methylurethanes from primary amines with dimethyl carbonate; Int Union Pure Applied Chemistry; Pure and Applied Chemistry; 77; 10; 10-2005; 1719-1725
dc.identifier0033-4545
dc.identifierhttp://hdl.handle.net/11336/55329
dc.identifier1365-3075
dc.identifierCONICET Digital
dc.identifierCONICET
dc.description.abstractThe mechanism of the reaction between amines with dimethyl carbonate (DMC) has been investigated. Whereas in the absence of bases, they give methylation and carboxymethylation reactions without selectivity (BAl2 and BAc2 mechanisms, respectively), in the presence of bases, the BAc2 mechanism prevails. The carbamate already formed reacts further with DMC via the BAl2 mechanism to give the corresponding N-methyl derivative. Such pronounced double selectivity has been explained in terms of Pearson’s Hard–Soft Acid-Base (HSAB) theory. Accordingly, N-methylcarbamates have been prepared from primary aliphatic and aromatic amines, either at reflux temperature of DMC (90 °C) or at 230 °C in autoclave. The reaction can be carried out in one step or through the isolation of the carbamate and the subsequent methylation reaction with DMC. This method is the direct synthesis, in high yield and selectivity, of secondary N-methylamines from the corresponding primary amines.
dc.languageeng
dc.publisherInt Union Pure Applied Chemistry
dc.relationinfo:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1351/pac200577101719
dc.relationinfo:eu-repo/semantics/altIdentifier/url/http://iupac.org/publications/pac/77/10/index.html
dc.rightshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectAmines
dc.subjectCarbamates
dc.subjectDimethyl Carbonate
dc.subjectGreen Chemistry
dc.subjectN-Methylamines
dc.titleDirect synthesis of N-methylurethanes from primary amines with dimethyl carbonate
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:ar-repo/semantics/artículo
dc.typeinfo:eu-repo/semantics/publishedVersion


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