Unidirectional triple and double hydrogen rearrangement reactions in the radical cations of gamma-arylalkanols

Kuck D, Filges U (1988)
Organic Mass Spectrometry 23(9): 643-653.

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Abstract
A novel fragmentation reaction accompanied by the unidirectional migration of three hydrogen atoms has been found in the radical cations of -arylpropanols with electron-donating substituents in the para position. This triple hydrogen (3H) rearrangement reaction is the dominant fragmentation channel of the long-lived molecular ions of trans-2-(4-dimethylaminobenzyl)-l-indanol, 2, but it occurs also in simpler -arylpropanol ions. Deuterium labelling of 2 reveals that the three hydrogen atoms originate with extraordinarily high specificity from the C(l), C(2) and O positions of the alcohol moiety. Cis- and 3-substituted isomers do not undergo this reaction. Along with the 3H rearrangement reaction a unidirectional double hydrogen (2H) rearrangement reaction takes place independently and with less specificity in the trans-2-(4-X-benzyl)-l-indanol ions 1+· and 2+·. No hydrogen exchange occurs during the 3H and 2H rearrangement reactions. Mechanistic alternatives of these unusual fragmentation reactions are discussed; the experimental evidence strongly favours pathways via several intermediate ion-neutral complexes.
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Kuck D, Filges U. Unidirectional triple and double hydrogen rearrangement reactions in the radical cations of gamma-arylalkanols. Organic Mass Spectrometry. 1988;23(9):643-653.
Kuck, D., & Filges, U. (1988). Unidirectional triple and double hydrogen rearrangement reactions in the radical cations of gamma-arylalkanols. Organic Mass Spectrometry, 23(9), 643-653.
Kuck, D., and Filges, U. (1988). Unidirectional triple and double hydrogen rearrangement reactions in the radical cations of gamma-arylalkanols. Organic Mass Spectrometry 23, 643-653.
Kuck, D., & Filges, U., 1988. Unidirectional triple and double hydrogen rearrangement reactions in the radical cations of gamma-arylalkanols. Organic Mass Spectrometry, 23(9), p 643-653.
D. Kuck and U. Filges, “Unidirectional triple and double hydrogen rearrangement reactions in the radical cations of gamma-arylalkanols”, Organic Mass Spectrometry, vol. 23, 1988, pp. 643-653.
Kuck, D., Filges, U.: Unidirectional triple and double hydrogen rearrangement reactions in the radical cations of gamma-arylalkanols. Organic Mass Spectrometry. 23, 643-653 (1988).
Kuck, Dietmar, and Filges, Ulrich. “Unidirectional triple and double hydrogen rearrangement reactions in the radical cations of gamma-arylalkanols”. Organic Mass Spectrometry 23.9 (1988): 643-653.
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