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Carbon skeletal rearrangements in 2‐phenylthiophene and 2,5‐diphenylthiophene under conditions of electron‐impact
Author(s) -
Weringa W. D.,
Sinnige H. J. M.,
Janssen Matthijs J.
Publication year - 1971
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.1210051207
Subject(s) - thiophene , scrambling , ion , chemistry , substituent , ring (chemistry) , carbon fibers , electron , crystallography , stereochemistry , materials science , physics , organic chemistry , philosophy , linguistics , composite number , composite material , quantum mechanics
The mass spectra of 13 C‐labelled 2‐phenylthiophenes and 2,5‐diphenylthiophenes were studied. The label distributions for the [HCS] + , [C 2 H 2 S] +· , [C 8 H 6 ] +· , [C 9 H 7 ] + and [C 7 H 5 ]S + ions from 2‐phenylthiophene and the [HCS] + , [C 9 H 7 ] + , [C 7 H 5 S] +· , and [C 15 H 11 ] + ions from 2,5‐diphenylthiophene were interpreted in terms of both carbon skeletal rearrangements in the thiophene ring and migration of the phenyl substituent. The degree of carbon scrambling in the thiophene ring appeared to be almost independent of the electron beam energy. The formation of some of the fragment ions studied seems to be so fast that no carbon scrambling could be detected at all; in neither case was complete scrambling of the carbon atoms of the thiophene ring observed.