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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 7, Number 4
August 20, 1963 

Study of 4-Nitroazoxybenzenes (Part Ⅱ) The Nature of α-and β-4-Nitroazoxybenzene in Strongly Acidic Solution

4-Nitroazoxybenzene에 관한 연구 (제2보) 강산 용액중에서의 α-및 β-4-Nitroazoxybenzene의 성질
Chi Sun Hahn

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 α-and β-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→1H bands of the spectra shown hyperchromic effect whereas the π→π* bands of them exhibit extream hypochromic effect, it appears most likely that trans → cis isomerization take place in the media. A mechanism of a triangular transition state by which the transformation might be proceeded, is proposed.
225 - 229
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