T11N3

Tandem high-resolution electrospray ionization mass spectrometry
of fluorinated thevinols and 18,19-dihydrothevinols

D.B. Eremin¹, V.I. Kadentsev¹, I.V. Sandulenko², S.K. Moiseev²

Fragmentations of fluorinated 18,19-dihydrothevinols and thevinols under electrospray ionization with collisionally activated dissociation accompanied by elimination of amine fragment from the cycle and further loss of H2O and CH3OH are investigated. For thevinol derivatives having a double bond at C18=C19, the [M+H]+ ions undergo retro-Diels–Alder fragmentation whose abundance depends on substituents at nitrogen and C20 atoms. Retro-Diels–Alder fragmentation of [M+H]+ ions of thevinols bearing groups –CH3, –CH2CH=CH2, –CH2– at nitrogen atom is due to the formation of protonated molecule of diene, whereas elimination of neutral diene in thevinols with hydrogen at N is observed.

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Keywords: T11N3 dihydrothevinols collisionally activated dissociation retro-Diels–Alder fragmentation tandem mass spectrometry thevinols electrospray/ionization

Categories: T11N3