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Mass Spectrometric Evidence for the Generation of Benzyne from Benzoyl Peroxide in Thermolysis

✍ Scribed by Ya-Ping Tu; Hu-Shan Yuan; Shu-Ying Liu

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 268 KB
Volume: 10
Category: Article
ISSN: 0951-4198
DOI: 10.1002/(sici)1097-0231(19960715)10:9<1093::aid-rcm628>3.0.co;2-s

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✦ Synopsis

Benzoyl peroxide gave rise to benzoic acid (at m/z 122) in its electron impact mass spectrum, and its perdeuterated counterpart produced perdeuterobenzoic acid, Cp,C02D, at m/z 128 under the same conditions. An intramolecular hydrogen abstraction is proposed for the formation of benzoic acid from the peroxide in thermolysis. As a result of this reaction, benzyne would be generated simultaneously. Anthracene was employed to trap any of the reactive intermediate benzyne. Collision-induced dissociation of the ion of m/z 254 from the mixture of benzoyl peroxide and anthracene indicated that triptycene was obtained by the trapping reaction, therefore confirming that benzyne is generated from benzoyl peroxide in thermolysis.

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