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Intermediates in the Dehydrogenation of Hydroaromatic Compounds with Quinones

✍ Scribed by Paul Müller; Daniel Joly

Publisher: John Wiley and Sons
Year: 1983
Tongue: German
Weight: 504 KB
Volume: 66
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19830660414

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✦ Synopsis

Abstract

Dehydrogenation of hydroaromatic compounds with quinones was reinvestigated in the light of recent criticism of the reaction mechanism. Kinetic and spectroscopic evidence shows that disappearance of substrate proceeds at the same rate as the product‐forming step. A mechanism consisting in fast formation followed by slow decomposition of an intermediate can be ruled out. The order of reactivities of 1,4‐cyclohexadiene (1), 1,4‐dihydronaphthalene (8) and 9,10‐dihydroanthracene (11) changes in going from benzoquinone to chloranil or 2,3‐dichloro‐5,6‐dicyanobenzoquinone. It is suggested that this behaviour could be due to contribution of CT‐complexes or HOMO‐LUMO interactions for determining the reactivity of the substrates.

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