Artículo
Abstract:
The reaction of ammonia with β-octa-O-acetylmaltose affords N,N′-diacetylmaltosylidenediamine (I), from which its acetate was prepared. A comparative study of the reaction in methanolic and in aqueous media was performed. The higher yield of I obtained in aqueous medium was qualitatively interpreted according to known kinetic studies about the reaction of ester ammonolysis, which is simultaneous and competitive with the reaction described. It is demonstrated that, in the reaction of penta-O-benzoyl-α-d-glucopyranose with methanolic ammonia, methyl benzoate is produced. Therefore, in that medium methoxide ions are formed, pointing out that, apart from the ammonolysis reaction and from the formation of “aldose–amides” by an ortho ester mechanism, a third competitive reaction takes place, by which acyl groups are split off through a transesterification mechanism. © 1963, American Chemical Society. All rights reserved.
Registro:
| Documento: | Artículo |
| Título: | The Reaction of Ammonia with Acylated Disaccharides. III. Acetyl Derivatives of Maltose and an Interpretation |
| Autor: | Cadenas, R.A.; Deferrari, J.O. |
| Filiación: | Laboratorio de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina |
| Año: | 1963 |
| Volumen: | 28 |
| Número: | 10 |
| Página de inicio: | 2613 |
| Página de fin: | 2616 |
| DOI: | http://dx.doi.org/10.1021/jo01045a031 |
| Título revista: | Journal of Organic Chemistry |
| Título revista abreviado: | J. Org. Chem. |
| ISSN: | 00223263 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v28_n10_p2613_Cadenas |
Citas:
---------- APA ----------
Cadenas, R.A. & Deferrari, J.O. (1963) . The Reaction of Ammonia with Acylated Disaccharides. III. Acetyl Derivatives of Maltose and an Interpretation. Journal of Organic Chemistry, 28(10), 2613-2616.http://dx.doi.org/10.1021/jo01045a031
---------- CHICAGO ----------
Cadenas, R.A., Deferrari, J.O. "The Reaction of Ammonia with Acylated Disaccharides. III. Acetyl Derivatives of Maltose and an Interpretation" . Journal of Organic Chemistry 28, no. 10 (1963) : 2613-2616.http://dx.doi.org/10.1021/jo01045a031
---------- MLA ----------
Cadenas, R.A., Deferrari, J.O. "The Reaction of Ammonia with Acylated Disaccharides. III. Acetyl Derivatives of Maltose and an Interpretation" . Journal of Organic Chemistry, vol. 28, no. 10, 1963, pp. 2613-2616.http://dx.doi.org/10.1021/jo01045a031
---------- VANCOUVER ----------
Cadenas, R.A., Deferrari, J.O. The Reaction of Ammonia with Acylated Disaccharides. III. Acetyl Derivatives of Maltose and an Interpretation. J. Org. Chem. 1963;28(10):2613-2616.http://dx.doi.org/10.1021/jo01045a031
