Abstract:2,2′,4,4′,6,6′-Hexamethylazoxybenzene (1) has been prepared and characterized. The u.v. spectrum is indicative of large distortion from coplanarity. 1 is only slightly more basic than azoxybenzene despite expectations due to electronic effect of the methyl substituents. Two factors are considered responsible for this: steric inhibition of resonance in the unprotonated species and steric hindrance to hydration in the conjugate acid.Rearrangement of 1 in moderately concentrated sulfuric acid gives rise to the al… Show more
The Wallach rearrangement is a strong acid promoted conversion of azoxybenzene and its derivatives into 4‐hydroxyazobenzene and the corresponding substituted hydroxyazobenzenes. The conversion under photo illumination is referred to as the photo‐Wallach rearrangement. The introduction of the hydroxyl group in the azoxybenzene series and naphthyl azoxy series has been discussed and compared it with the photo‐Wallach rearrangement conditions. This reaction has general application in the preparation of hydroxyazobenzenes and hydroxyazonaphthalenes.
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