Abstract
AbstractIn 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 isopentyl 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.
Published Version
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