Issue 18, 1970

Mass spectrometry of organic compounds. Part V. Mass spectra of substituted aroylhydrazones

Abstract

The mass spectra of a number of substituted aroylhydrazones, ArCO·NH·N[double bond, length as m-dash]C(R)Ar′ where R = H or alkyl, are reported. Fragmentation of the hydrazones with R = H is dominated by paths leading to the ions ArCO+′ArCO·NH2, and Ar′CN, and evidence is presented that the hydrogen rearrangement to form ArCO·NH2 proceeds via a four-membered transition state. Formation of the ion ArCN was shown to be due to thermal decomposition of the hydrazones in the ion chamber. Hydrazones with R = alkyl and two diaroylhydrazones, ArCO(Ar′CO)N·N[double bond, length as m-dash]CHPh, were found to undergo skeletal rearrangement in addition to simple bond cleavage.

Article information

Article type
Paper

J. Chem. Soc. C, 1970, 2574-2577

Mass spectrometry of organic compounds. Part V. Mass spectra of substituted aroylhydrazones

D. G. I. Kingston, H. P. Tannenbaum, G. B. Baker, J. R. Dimmock and W. G. Taylor, J. Chem. Soc. C, 1970, 2574 DOI: 10.1039/J39700002574

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