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Aromatisation of Six-Membered Rings

Aromatization of Six-Membered Rings: Oxidation with Quinone

In this reaction, quinones are reduced to the corresponding hydroquinones. Mechanistically, a hydride anion is transferred to a quinone oxygen atom, followed by addition of a proton to the the newly formed phenolate anion. Alternatively, electron transfer mechanisms are being discussed.

Fig.1

Electron-poor quinones, such as chloranil (2,3,5,6-tetrachloro-1,4-benzoquinone) and DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) are especially reactive with the latter a better substrate than the former.

Fig.2
Fig.3
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