582-85-4Relevant academic research and scientific papers
Facile Photorearrangement of Some Crowded Azoxyarenes via Two Concurrent Pathways
Okubo, Masao,Hyakutake, Hayato,Taniguchi, Naoki
, p. 3005 - 3007 (2007/10/02)
Naphthalene-1-ONN-azoxybenzenes and some unsymmetrically ortho-substituted ONN- and NNO-azoxybenzenes were prepared, and their photochemical behavior in ethanol was compared.The crowded azoxyarenes tend to undergo a facile Wallach rearrangement via the known azoxy-ortho oxygen migration and a concurrent pathway involving ONN-NNO-isomerization.The relative contribution of the two pathways was affected by substituents.
Studies on the Reactivity of Azoxybenzenes. Part 12. αβ-Interconversion of para-Monosubstituted Azoxybenzenes in the Wallach Rearrangement
Yamamoto, Jiro,Aimi, Hironori,Masuda, Yasuko,Sumida, Takashi,Umezo, Masahiro,Matuura, Teruo
, p. 1565 - 1568 (2007/10/02)
Under the reaction conditions for the Wallach rearrangement, 4-methyl-ONN-(1α), 4-methyl-NNO-(1β), 4-nitro-ONN-(2α), and 4-nitro-NNO-azoxybenzene (2β) were found to undergo αβ-interconversion, while 4-bromo-ONN-(3α) and 4-bromo-NNO-azoxybenzene (3β) do not.The αβ-interconversion occurs with both mono- and di-protonated forms of the azoxybenzenes.
SYNTHESIS OF AZOXYBENZENE-SbCl5 COMPLEXES AND THEIR SELECTIVE ORTHO-WALLACH REARRANGEMENT
Yamamoto, Jiro,Nishigaki, Yukihiro,Umezu, Masahiro,Matsuura, Teruo
, p. 3177 - 3180 (2007/10/02)
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.
