Organic Mass Spectrometry p. 42 - 47 (1988)
Update date:2022-08-03
Topics:
Kingston, Eric E.
Eichholzer, John V.
Lyndon, Paul
MacLeod, John K.
Summons, Roger E.
In contradiction of long-accepted mass spectrometric dogma, the site-specific γ-hydrogen rearrangement is observed in alkylbenzenes in which both ortho positions are blocked with methyl substituents.Mass spectrometric studies of a series of five trimethyl- and three tetramethylisopentylbenzenes have shown that this rearrangement is only suppressed to a significant degree in those compounds in which all three positions ortho and para to the isopenyl group are blocked.Deuterium labelling has confirmed the γ-site-specific origin of the migrating H atom while metastable studies have been used to investigate the mechanism of the rearrangement process.
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Doi:10.1055/s-0028-1088202
(2009)Doi:10.1021/jm201512x
(2012)Doi:10.1007/BF00763381
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(1965)Doi:10.1007/BF00810642
(1987)Doi:10.1021/jo00261a027
(1988)