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Radical-induced aromatic substitution between benzoyl peroxide and benzenediols in the gas phase characterized by mass spectrometry

✍ Scribed by Ya-Ping Tu; Ya-Qin Liu

Publisher: John Wiley and Sons
Year: 1992
Tongue: English
Weight: 333 KB
Volume: 27
Category: Article
ISSN: 1076-5174
DOI: 10.1002/oms.1210270325

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✦ Synopsis

A radical-induced aromatic substitution mechanism for the reaction between benzoyl peroxide and benzenediols in the gas phase was characterized by mass spectrometry. The benzoyloxy radical produced from the hornolysis of benzoyl peroxide associates at its carbonyl group with the phenolic hydroxyl group. The pairing tendency of the unpaired electron on the oxygen of the radical induces electron transfer along the hydrogen bond, which results in the rupture of the 0-H bond of the phenol and aromatic substitution at the ortho position of the benzoyloxy radical. Supporting evidence for the mechanism was obtained by isotope labelling.

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