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Abstract:

Some 3-glycosyl-5-aryl-2-isoxazolines were studied in the gas phase under electron ionization (EI) conditions in order to elucidate their behavior. These derivatives showed an interesting rearrangement involving opening of the heterocyclic ring with a concomitant ring closing to afford a new isoxazoline derivative. The first step of this reaction was the less common cleavage of the heterocyclic C(5)-O bond. The 5-aryl substituent was responsible for the pseudobenzylic stabilization of the new isoxazoline derivative. EI tandem mass spectrometry and EI high-resolution mass spectrometry allowed the elucidation of fragmentation pathways.

Registro:

Documento: Artículo
Título:A novel rearrangement in the gas phase under electron ionization for 3-glycosyl-5-aryl-2-isoxazolines
Autor:D'Accorso, N.; Fascio, M.; Arabehety, C.G.; Seldes, A.M.
Filiación:Depto. de Quim. Orgánica, Fac. de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina
U. Microanalisis y Metodos F., Depto. de Quim. Orgánica, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina
Lab. Nacional de Análisis, Servicios Espectrometria Masa A., Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina
Palabras clave:3-glycosyl-5-aryl-2-isoxazolines; Electron ionization; Rearrangement; Tandem mass spectrometry; isoxazole derivative; article; ionization; mass spectrometry; priority journal; tandem mass spectrometry
Año:1999
Volumen:34
Número:9
Página de inicio:915
Página de fin:921
DOI: http://dx.doi.org/10.1002/(SICI)1096-9888(199909)34:9<915::AID-JMS850>3.0.CO;2-A
Título revista:Journal of Mass Spectrometry
Título revista abreviado:J. Mass Spectrom.
ISSN:10765174
CODEN:JMSPF
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10765174_v34_n9_p915_DAccorso

Referencias:

  • Kozikowski, A.P., (1984) Acc. Chem. Res., 17, p. 410
  • Fascio, M.L., D'Accorso, N.B., (1996) J. Heterocycl. Chem., 33, p. 1573
  • Sutharchanadevi, M., Murugan, R., (1996) Comprehensive Heterocyclic Chemistry, 3, p. 44. , Katritzky AR, Rees CW, Scriven EFV (ed). Elsevier Applied Science, London
  • Grünanger, P., Vita-Finzi, P., (1991) Heterocyclic Compounds, 49 (PART 1), p. 441. , Wiley: New York
  • Fascio, M., Montesano, V., D'Accorso, N., to be published; Massyn, C., Cambon, A., (1975) J. Fluorine Chem., 5, p. 67
  • Fascio, M., Montesano, V., D'Accorso, N., (1998) J. Heterocycl. Chem., 35, p. 104

Citas:

---------- APA ----------
D'Accorso, N., Fascio, M., Arabehety, C.G. & Seldes, A.M. (1999) . A novel rearrangement in the gas phase under electron ionization for 3-glycosyl-5-aryl-2-isoxazolines. Journal of Mass Spectrometry, 34(9), 915-921.
http://dx.doi.org/10.1002/(SICI)1096-9888(199909)34:9<915::AID-JMS850>3.0.CO;2-A
---------- CHICAGO ----------
D'Accorso, N., Fascio, M., Arabehety, C.G., Seldes, A.M. "A novel rearrangement in the gas phase under electron ionization for 3-glycosyl-5-aryl-2-isoxazolines" . Journal of Mass Spectrometry 34, no. 9 (1999) : 915-921.
http://dx.doi.org/10.1002/(SICI)1096-9888(199909)34:9<915::AID-JMS850>3.0.CO;2-A
---------- MLA ----------
D'Accorso, N., Fascio, M., Arabehety, C.G., Seldes, A.M. "A novel rearrangement in the gas phase under electron ionization for 3-glycosyl-5-aryl-2-isoxazolines" . Journal of Mass Spectrometry, vol. 34, no. 9, 1999, pp. 915-921.
http://dx.doi.org/10.1002/(SICI)1096-9888(199909)34:9<915::AID-JMS850>3.0.CO;2-A
---------- VANCOUVER ----------
D'Accorso, N., Fascio, M., Arabehety, C.G., Seldes, A.M. A novel rearrangement in the gas phase under electron ionization for 3-glycosyl-5-aryl-2-isoxazolines. J. Mass Spectrom. 1999;34(9):915-921.
http://dx.doi.org/10.1002/(SICI)1096-9888(199909)34:9<915::AID-JMS850>3.0.CO;2-A