Add time:08/30/2019 Source:sciencedirect.com
The MS/MS spectrum of the metastable molecular ions of DIMETHYL TEREPHTHALATE (cas 120-61-6) 1 features an unexpected, quite intense, loss of a methyl radical. Using a combination of mass spectrometry techniques, it is shown that this process consists of a pseudo simple cleavage reaction isomerizing, in the first step, one of the two methoxycarbonyl substituents into a distonic ArC+(–OH)–OCH2 (Ar = CH3O2C–C6H4–) connectivity. The final product is established to be protonated 5-carboxyphthalide. The overall mechanism of the methyl loss includes a sequence of five steps as supported by quantum chemical (DFT) calculations.
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