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Aryl versus alkyl and vinyl migration in the mass spectra of sulphone derivatives
Author(s) -
Soothill Rayner J.,
Williams L. R.
Publication year - 1972
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.1210061012
Subject(s) - chemistry , alkyl , fragmentation (computing) , aryl , mass spectrum , medicinal chemistry , ion , polymer chemistry , molecule , yield (engineering) , sulfur , organic chemistry , materials science , computer science , metallurgy , operating system
The 2‐acetoxyethyl aryl sulphones were found to be unsuitable for a comparative study with the corresponding chlorides and alcohols as their predominant fragmentation involved cleavage of the aliphatic carbon‐sulphur bond with charge retention on the aliphatic part of the molecule The expected McLafferty rearrangement to yield an intermediate vinyl species was only a minor fragmentation path. Indirect evidence for alkyl migration in the molecular ion was found in the spectrum of 2‐acetoxyethyl 1‐paranitro phenyl sulphone. The spectra of the aryl vinyl sulphones revealed intense [Aryl SO]+ ions resulting from preferred migration of the vinyl group from sulphur to oxygen.