502916-43-0Relevant articles and documents
3-Aroyl-5-hydroxyflavones: Synthesis and mechanistic studies by mass spectrometry
Cardoso, Ana M.,Silva, Artur M. S.,Barros, Cristina M. F.,Almeida, Lucia M. P. M.,Ferrer-Correia,Cavaleiro, Jose A. S.
, p. 930 - 939 (1997)
The synthesis and mass spectra of three 3-aroyl-5-hydroxflavones are reported. The interpretation of the mechanistic pathways for the fragmentation of the metastable molecular ions of these compounds was achieved through the analysis of their mass-analysed ion kinetic energy (MIKE) spectra and of the B2/E spectra of a few fragment ions. Labelling of the hydroxyl proton with deuterium and the analysis of the MIKE spectra of a model compound with chlorine atoms in the 2',6'- and 2',6'-positions led to a mechanism for the losses of OH. and HCO. which involves hydrogen migration from the 2'- or 6'-position to the 6-carbonyl oxygen atom. A mechanism for the loss of a neutral molecule of anisole from the molecular ion of the 3-aroyl-5-hydroxyflavone with a methoxyl group in the 4'- and 4'-positions is also suggested. For the flavones with hydrogen or chlorine substituents at these positions, loss of a phenyl (or chlorophenyl) radical occurs instead.