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Mass spectrometry of cycloheptatriene derivatives. III —skeletal rearrangements in the molecular ion of 7‐cyano‐7‐methylcycloheptatriene and in some of its fragment ions
Author(s) -
Venema A.,
Nibbering N. M. M.
Publication year - 1974
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.1210091214
Subject(s) - cycloheptatriene , ion , chemistry , deuterium , mass spectrometry , labelling , polyatomic ion , molecule , computational chemistry , stereochemistry , organic chemistry , chromatography , atomic physics , physics , biochemistry
It is shown by carbon and deuterium labelling experiments that a substantial part of the molecular ions of 7‐cyano‐7‐methylcycloheptatriene has rearranged to a tolylacetonitrile, both in the ion source and in the second field free region. The evidence follows from a comparative study of α‐methylbenzylcyanide, o ‐ and p ‐tolylacetonitriles and their labelled analogues. The decomposing [M — CH 3 ] + ion from 7‐cyano‐7‐methylcycloheptatriene presumably has a cyanomethylphenyl cation, instead of a cyanotropylium structure.