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Skeletal rearrangements in mass spectra. Part I. Bis‐aryl compounds
Author(s) -
Wszolek P. C.,
McLafferty F. W.,
Brewster J. H.
Publication year - 1968
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210010112
Subject(s) - chemistry , moiety , aryl , mass spectrum , spectral line , azobenzene , polarizability , photochemistry , medicinal chemistry , crystallography , stereochemistry , molecule , organic chemistry , ion , alkyl , physics , astronomy
Examination of a large number of spectra indicates that bis‐unsaturated compounds commonly undergo a skeletal rearrangement in which part or all or the bridging moiety is eliminated, often with concomitant loss of hydrogen atoms. The spectra of labeled azobenzene, diphenyl sulfide, and their p , p ′‐dimethyl derivatives show that scrambling of hydrogen atoms precedes or accompanies such rearrangements, in contrast to the loss of a p ‐methyl group from the latter derivatives. These results are rationalized in terms of the radical site formed on one unsaturated functional group attacking the polarizable π‐electrons of the other unsaturated group.