Archiv der Pharmazie p. 751 - 760 (1992)
Update date:2022-08-04
Topics:
Striegel
Mayer
Wiegrebe
Schlunegger
Siegrist
Aebi
In the gas phase, the phenyl-2-propanone molecules 2a-4a lose upon electron impact chloro-, bromo-, and iodo-radicals specifically at the orthopOsition of the phenyl group giving rise to strong (M-Hal.)+-ions (70/12 eV; 1st and 2nd FFR) of identical structure as confirmed by their MIKE-CAD-spectra. The daughter ions at m/z 133 from o-chlorophenyl-2-propanone (2a) and 2,2-dimethyl-2,3-dihydro[b]furane (11) are structurally similar but not identical (similarity index 99.8). The collisionally activated (2nd FFR) (M-Br.)+-ions from o-bromophenyl-2-propanone (3a) and 1-bromo-1-phenyl-2-propanone (12) produce virtually congruent spectra. The most impOrtant subsequent fragmentation of the (M-Hal-)+-ions from 2a-4a is the loss of CO which incorporates the C-atom of the carbonyl group exclusively (13C labelling). Mechanistic aspects of the fragmentation sequences are discussed (Figs. 5 and 8).
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Doi:10.1039/DT9930000625
(1993)Doi:10.1002/adsc.201300271
(2013)Doi:10.1016/S0040-4039(00)61663-5
(1993)Doi:10.1021/ja01156a086
(1951)Doi:10.1021/jm00046a016
(1994)Doi:10.1021/jm020094i
(2002)