Study of 4-Nitroazoxybenzenes (Part II) The Nature of $\alpha$-and $\beta$-4-Nitroazoxybenzene in Strongly Acidic Solution

4-Nitroazoxybenzene에 關한 硏究 (第2報) 强酸 溶液中에서의 $\alpha$- 및 $\beta$-4-Nitroazoxybenzene의 性質

  • Published : 19631200

Abstract

The nature of the two isomers of 4-nitroazoxybenzenes in strongly acidic solution have been analyzed by U.V. spectrophotometry. Oxygen atom in the azoxy-group of $\alpha$-and $\beta$-4-nitroazoxybenzene in strong acid solution migrates neither to para position nor ortho position of the unsubstituted benzene ring of the compound in contrast with the cases of methyl-and bromo-substituted azoxybenzene, and shown no Wallach rearrangement. Since the $^1A{\rightarrow}^1H$ bands of the spectra shown hyperchromic effect whereas the ${\pi}{\rightarrow}{\pi}^*$ bands of them exhibit extream hypochromic effect, it appears most likely that trans ${\rightarrow}$cis isomerization take place in the media. A mechanism of a triangular transition state by which the transformation might be proceeded, is proposed.

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References

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