We report a method to convert substituted tropylium ions into benzenoid derivatives.
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Electrospray ionization tandem mass spectrometry of 4-aryl-3,4-dihydrocoumarins.
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Department of Chemistry, Faculty of Philosophy, Science and Letters at Ribeirão Preto, University of São Paulo, Ribeirão Preto, Brazil.
We have investigated the gas-phase fragmentation reactions of 11 synthetic 4-aryl-3,4-dihydrocoumarins by electrospray ionization tandem mass spectrometry (ESI-MS/MS) on a quadrupole-time-of flight (Q-TOF) hybrid mass spectrometer. We have also estimated thermochemical data for the protonated coumarins (precursor ion A) and product ion structures by computational chemistry at a B3LYP level of theory to establish the ion structures and to rationalize the fragmentation pathways. The most abundant ions in the product ion spectra of coumarins 1-11 resulted from CHO, CO, CHO, CHO, CHO, and CHOH eliminations through retro-Diels-Alder (RDA) reactions, remote hydrogen rearrangements (β-eliminations), and β-lactone ring contraction.
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School of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South Africa.
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Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore, India.
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