Mostrar el registro sencillo del ítem
dc.contributor.author
Tundo, Pietro
dc.contributor.author
Bressanello, Salimo
dc.contributor.author
Loris, Alessandro
dc.contributor.author
Sathicq, Angel Gabriel
dc.date.available
2018-08-14T14:10:28Z
dc.date.issued
2005-10
dc.identifier.citation
Tundo, 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.identifier.issn
0033-4545
dc.identifier.uri
http://hdl.handle.net/11336/55329
dc.description.abstract
The 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.format
application/pdf
dc.language.iso
eng
dc.publisher
Int Union Pure Applied Chemistry
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Amines
dc.subject
Carbamates
dc.subject
Dimethyl Carbonate
dc.subject
Green Chemistry
dc.subject
N-Methylamines
dc.subject.classification
Otras Ciencias Químicas
dc.subject.classification
Ciencias Químicas
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
dc.title
Direct synthesis of N-methylurethanes from primary amines with dimethyl carbonate
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2018-08-08T14:55:04Z
dc.identifier.eissn
1365-3075
dc.journal.volume
77
dc.journal.number
10
dc.journal.pagination
1719-1725
dc.journal.pais
Estados Unidos
dc.description.fil
Fil: Tundo, Pietro. Universita' Ca' Foscari Di Venezia; Italia
dc.description.fil
Fil: Bressanello, Salimo. Universita' Ca' Foscari Di Venezia; Italia
dc.description.fil
Fil: Loris, Alessandro. Universita' Ca' Foscari Di Venezia; Italia
dc.description.fil
Fil: Sathicq, Angel Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
dc.journal.title
Pure and Applied Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1351/pac200577101719
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://iupac.org/publications/pac/77/10/index.html
Archivos asociados