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The electron ionization mass spectra of nine muconic acid dimethyl esters that bear up to three muconate groups fused with a centropolycyclic di-, triand hexaquinane framework exhibit dominating fragmentation by loss of a methoxycarbonyl radical, COOMe, from the molecular radical cations, M. Pyrylio-annelated structures for the [M – COOMe] ions are postulated in analogy to literature reports on simple muconic acids esters. The congeners bearing two or three dimethyl muconate groups lose also two COOMe radicals after twofold ionization. The doubly charged fragment ions [M  2 COOMe] are proposed to contain two isolated pyrylium rings fused to the original trior hexaquinane core, thus representing polyaromatic distonic dications.

Mass spectrometric fragmentation of di-, tri-, and hexaquinane-fused dimethyl muconates induced by single and double electron ionization