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The mass spectral rearrangements of aryl propenyl sulfones. An electron impact induced smiles type rearrangement
Author(s) -
Hill Charlotte J.,
Thyagarajan B. S.,
Bates D. K.,
Spangler R. J.
Publication year - 1977
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.1210120608
Subject(s) - sulfone , chemistry , aryl , propene , propenyl , mass spectrum , medicinal chemistry , cis–trans isomerism , smiles rearrangement , mass spectrometry , stereochemistry , organic chemistry , catalysis , alkyl , chromatography
The mass spectral behavior of trans ‐1‐arylsulfonyl‐2‐arylsulfenyl‐propenes, trans ‐1‐arylsulfonyl‐2‐arylsulfinyl‐propenes and trans ‐1, 2‐(arylsulfonyl)‐propenes was examined. A Smiles type rearrangement was present in the sulfonyl‐sulfides, but was completely absent in the trans ‐1‐arylsulfonyl‐2‐arylsulfinyl‐propenes and trans‐1, 2‐(arylsulfonyl)‐propenes. Vinyl migration to the sulfone oxygen predominates over aryl migration in all of the compounds studied. The mass spectra of the cis and trans isomers of 1‐ p ‐tolylsulfenyl‐2‐ p ′‐tolysulfonyl‐propene and 1, 2‐( p ‐tolylsulfonyl)‐propene are also described.