Artículo
Vázquez, A.; Nudelman, N.S. "Complex intermediates in the NO insertion reactions into lithium amides" (2006) Journal of Physical Organic Chemistry. 19(11):748-751
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Abstract:
Nitric oxide (NO) is known to produce the carcinogenetic nitrosamines but it has also been recently reported, both as a regulator of many important physiological functions and as a possible pharmaceutical delivery system. The present paper describes the NO insertion into N - Li bond of lithium amides, to afford very good to almost quantitative yields of N-nitrosamines. A study of the reaction intermediate suggested a further advantage of this synthetic methodology, widening its scope to its use in tandem reactions. Thus, in situ addition of an organolithium reagent into the N=O bond leads to an almost quantitative conversion into the corresponding hydrazone. This compound could further add a second equivalent of the same (or another) organolithium affording substituted hydrazines. The hydrazines thus prepared have a potential chiral carbon, by running the reaction in the presence of a chiral auxiliary, enantiomeric excess could be obtained. By reducing the compound with Raney Ni, the scope of this methology could be enlarged for the potential preparation of chiral primary amines, project that is currently under progress. Copyright © 2006 John Wiley & Sons, Ltd.
Registro:
| Documento: | Artículo |
| Título: | Complex intermediates in the NO insertion reactions into lithium amides |
| Autor: | Vázquez, A.; Nudelman, N.S. |
| Filiación: | Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, P 3 Ciudad Universitaria, (1428), Buenos Aires, Argentina |
| Palabras clave: | Hydrazones; Lithium amides; Nitrosamines; NO insertion; Tandem reactions; Chemical bonds; Drug products; Nitric oxide; Organometallics; Physiology; Reaction kinetics; Hydrazones; Lithium amides; NO insertion; Tandem reactions; Nitrosamines |
| Año: | 2006 |
| Volumen: | 19 |
| Número: | 11 |
| Página de inicio: | 748 |
| Página de fin: | 751 |
| DOI: | http://dx.doi.org/10.1002/poc.1069 |
| Título revista: | Journal of Physical Organic Chemistry |
| Título revista abreviado: | J Phys Org Chem |
| ISSN: | 08943230 |
| CODEN: | JPOCE |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_08943230_v19_n11_p748_Vazquez |
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Citas:
---------- APA ----------
Vázquez, A. & Nudelman, N.S. (2006) . Complex intermediates in the NO insertion reactions into lithium amides. Journal of Physical Organic Chemistry, 19(11), 748-751.http://dx.doi.org/10.1002/poc.1069
---------- CHICAGO ----------
Vázquez, A., Nudelman, N.S. "Complex intermediates in the NO insertion reactions into lithium amides" . Journal of Physical Organic Chemistry 19, no. 11 (2006) : 748-751.http://dx.doi.org/10.1002/poc.1069
---------- MLA ----------
Vázquez, A., Nudelman, N.S. "Complex intermediates in the NO insertion reactions into lithium amides" . Journal of Physical Organic Chemistry, vol. 19, no. 11, 2006, pp. 748-751.http://dx.doi.org/10.1002/poc.1069
---------- VANCOUVER ----------
Vázquez, A., Nudelman, N.S. Complex intermediates in the NO insertion reactions into lithium amides. J Phys Org Chem. 2006;19(11):748-751.http://dx.doi.org/10.1002/poc.1069
