Research Article

Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase

  1. Martha S. Morales-Ríos1,2,*,
  2. Perla Y. López-Camacho1,2,
  3. Carlos O. Jacobo-Cabral1,2,
  4. Nadia A. Pérez-Rojas1,
  5. Joel J. Trujillo-Serrato1,
  6. Eleuterio Burgueño-Tapia3,
  7. Oscar R. Suárez-Castillo4,
  8. Pedro Joseph-Nathan1,2

Article first published online: 18 APR 2011

DOI: 10.1002/jms.1915

Issue

Journal of Mass Spectrometry

Journal of Mass Spectrometry

Volume 46, Issue 5, pages 489–495, May 2011

Additional Information

How to Cite

Morales-Ríos, M. S., López-Camacho, P. Y., Jacobo-Cabral, C. O., Pérez-Rojas, N. A., Trujillo-Serrato, J. J., Burgueño-Tapia, E., Suárez-Castillo, O. R. and Joseph-Nathan, P. (2011), Unimolecular rearrangements of ketene-O,O-acetals and fragmentations occurring in the gas phase. J. Mass Spectrom., 46: 489–495. doi: 10.1002/jms.1915

Author Information

  1. 1

    Departamento de Química Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, México, D. F., 07000 Mexico

  2. 2

    Programa de Posgrado en Farmacología, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, México, D. F., 07000 Mexico

  3. 3

    Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala, Col. Santo Tomás, México, D. F., 11340 Mexico

  4. 4

    Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, Mineral de la Reforma, Hidalgo, 42184 Mexico

*Departamento de Química and Programa de Posgrado en Farmacología, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, México, D. F., 07000 Mexico.

Publication History

  1. Issue published online: 13 APR 2011
  2. Article first published online: 18 APR 2011
  3. Manuscript Accepted: 15 MAR 2011
  4. Manuscript Received: 14 FEB 2011

Funded by

  • CONACYT. Grant Number: 81810

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Keywords:

  • ketene acetal;
  • gas phase rearrangement;
  • thermal decarbomethoxylation;
  • indole;
  • EI-ion trap

Abstract

Gas phase skeletal rearrangements of regioisomeric 3-cyano-2-methoxy-3a-alkylfuro[2,3-b]- and [3,2-b]indoles were evidenced by product ions [M − 32]+•, consistent with loss of methanol, on electron ionization in their mass spectra. The rearranged products occurring in gas phase were demonstrated to have elemental composition and fragmentation properties identical to those of authentic samples of 2-indolyl cyanomalonates. Isotopic labeling experiments support the formation mechanism of the [M − 32]+• ion. Additional thermal gas-phase reaction products were characterized by comparison with an authentic sample. Copyright © 2011 John Wiley & Sons, Ltd.

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