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- W2006010247 abstract "N-(2-Propynyl)anilines undergo amino-Claisen rearrangement to a minor extent in the ion source, losing a molecule of HCN under electron impact conditions. However, metastable molecular ions with energies closer to threshold undergo Claisen rearrangement giving rise to more abundant [M − HCN]+· ions in the first field-free region. Loss of a hydrogen from the molecular ion gives rise to the base peak in the mass spectrum of N-(2-propynyl)aniline. The hydrogen that is expelled for the formation of the [M − H]+ ion is observed to be from the amino nitrogen, propargylic carbon and the ortho-carbon of the ring. The last process leads to a cyclic fragment involving intramolecular aromatic substitution. Double oxygen migration from the nitro group to the triple bond, due to the ortho effect, yields an abundant ion at m/z 105 in N-(2-propynyl)-o-nitroaniline. The proposed fragmentation pathways and ion structures are substantiated by high-resolution data, B/E and B2/E linked-scan spectra, collisionally activated dissociation–B/E linked-scan spectra and deuterium isotopic labelling." @default.
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- W2006010247 date "1995-07-01" @default.
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- W2006010247 title "Intramolecular aromatic substitution and amino-Claisen rearrangement in substitutedN-(2-propynyl)anilines on electron impact" @default.
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- W2006010247 doi "https://doi.org/10.1002/jms.1190300713" @default.
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