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Pinacol rearrangement of quinoline analogs of benzopinacol and evidence for rearrangement under the conditions of electron impact
Author(s) -
Brown Ellis V.,
Frazer Marshall G.
Publication year - 1969
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570060418
Subject(s) - chemistry , mass spectrum , quinoline , pinacol , medicinal chemistry , electron ionization , stereochemistry , mass spectrometry , organic chemistry , chromatography , catalysis , ion , ionization
The pinacols, 1,2‐di(2‐quinolyl)‐1,2‐diphenylethane‐1,2‐diol and 1,2‐di(8‐quinolyl)‐1,2‐diphenylethane‐1,2‐diol, were prepared and rearranged. The mass spectrum of the phenyl‐2‐quinolylpinacolone showed fragment peaks corresponding to the pinacolone resulting from 2‐quinolyl migration. The mass spectrum of the phenyl‐8‐quinolylpinacolone showed fragment peaks corresponding to the pinacolone resulting from phenyl migration. Evidence for the rearrangement by electron impact was observed in the mass spectrum of each pinacol.