Destabilized carbenium ions: [alpha]-imidoyl carbenium ions and the electron impact mass spectra of [alpha]-haloaldimines and [alpha]-haloketimines

Sürig T, Grützmacher H-F, De Kimpe N (1991)
Organic Mass Spectrometry 26(10): 882-888.

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A series of alpha-chloro- and alpha-bromoketimines compounds (1-9) with different substituents at the alpha-position and at the imino group has been investigated by electron impact mass spectrometry as possible precursors of the correspondingly substituted alpha-imidoyl carbenium ion, an important class of destabilized carbenium ions. The main fragmentation of the molecular ions of compounds 1-9 in the ion source corresponds to an alpha-cleavage at the imino group; however, fragment ions are also formed by loss of the alpha-halo substituent. These fragment ions correspond at least formally to alpha-imidoyl carbenium ions. Their further reactions in dependence on the type of substituents at the imino group and at the alpha-C atom, were studied by mass-analysed ion kinetic energy and collisional activation mass spectrometry. The results agree with the initial formation of destabilized alpha-imidoyl carbenium ions but indicate an easy rearrangement of these ions in the presence of suitable alkyl substituents by 1,2- and 1,4-hydrogen shifts to more stable isomers.
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Sürig T, Grützmacher H-F, De Kimpe N. Destabilized carbenium ions: [alpha]-imidoyl carbenium ions and the electron impact mass spectra of [alpha]-haloaldimines and [alpha]-haloketimines. Organic Mass Spectrometry. 1991;26(10):882-888.
Sürig, T., Grützmacher, H. - F., & De Kimpe, N. (1991). Destabilized carbenium ions: [alpha]-imidoyl carbenium ions and the electron impact mass spectra of [alpha]-haloaldimines and [alpha]-haloketimines. Organic Mass Spectrometry, 26(10), 882-888.
Sürig, T., Grützmacher, H. - F., and De Kimpe, N. (1991). Destabilized carbenium ions: [alpha]-imidoyl carbenium ions and the electron impact mass spectra of [alpha]-haloaldimines and [alpha]-haloketimines. Organic Mass Spectrometry 26, 882-888.
Sürig, T., Grützmacher, H.-F., & De Kimpe, N., 1991. Destabilized carbenium ions: [alpha]-imidoyl carbenium ions and the electron impact mass spectra of [alpha]-haloaldimines and [alpha]-haloketimines. Organic Mass Spectrometry, 26(10), p 882-888.
T. Sürig, H.-F. Grützmacher, and N. De Kimpe, “Destabilized carbenium ions: [alpha]-imidoyl carbenium ions and the electron impact mass spectra of [alpha]-haloaldimines and [alpha]-haloketimines”, Organic Mass Spectrometry, vol. 26, 1991, pp. 882-888.
Sürig, T., Grützmacher, H.-F., De Kimpe, N.: Destabilized carbenium ions: [alpha]-imidoyl carbenium ions and the electron impact mass spectra of [alpha]-haloaldimines and [alpha]-haloketimines. Organic Mass Spectrometry. 26, 882-888 (1991).
Sürig, Thomas, Grützmacher, Hans-Friedrich, and De Kimpe, Norbert. “Destabilized carbenium ions: [alpha]-imidoyl carbenium ions and the electron impact mass spectra of [alpha]-haloaldimines and [alpha]-haloketimines”. Organic Mass Spectrometry 26.10 (1991): 882-888.
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