SYNTHESIS OF AZOXYBENZENE-SbCl5 COMPLEXES AND THEIR SELECTIVE ORTHO-WALLACH REARRANGEMENT

Article abstract of DOI:10.1016/0040-4020(80)80162-1

When an equimolar solution of various azoxybenzenes and SbCl5 in carbon tetrachloride were mixed, a 1:1 complex immediately deposited as orange crystals in high yield.The thermal reaction of these complexes in inert solvents gives o-hydroxy-azobenzene selectively.On the contrary, other Lewis acids, such as TiCl4, AlCl3, FeCl3 and ZnBr2 failed to give an isolatable complex with azoxybenzene, and their direct thermal reaction with azoxybenzene resulted in deoxygenation to yield azobenzene as a main product.