The mass spectra of diaziridinones |
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Authors: | Istvn Lengyel Frederick D Greene Jos F Pazos |
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Institution: | István Lengyel,Frederick D. Greene,José F. Pazos |
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Abstract: | The electron-impact induced fragmentation of four N,N′-di-t-alkyl-substituted diaziridinones (I to IV) has been studied by both conventional and high resolution mass spectrometry. All diaziridinones exhibit weak molecular ions. Ejection of an alkyl isocyanate, corresponding to the N-alkyl substituent, from the molecular ion, is a dominant and general fragmentation process. Isocyanate-type odd-electron fragment ions occur only in III and IV (where at least one R group is phenyl) and are of low abundance. Elimination of a hydrocarbon radical from the tertiary alkyl substituents is observed in all compounds investigated. McLafferty rearrangement with elimination of a neutral alkene occurs in all compounds. Abundant even-electron hydrocarbon ions corresponding to the mass of the N-alkyl substituent are prevalent. The complete absence of elimination of carbon monoxide is noted. Loss of oxygen from the M ? RCH2]+ species has been confirmed by accurate mass measurement. Several remarkable rearrangement reactions have been uncovered by high resolution studies and deuteration experiments. |
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