The normal and the retro-Boulton-Katritzky rearrangement of hydroxy- and nitro-substituted benzofuroxans

The demethylation of 7-methoxy-4-nitrobenzofuroxan by aqueous KOH gives rise to 7-hydroxy-4-nitrobenzofuroxan as well as 5-hydroxy-4-nitrobenzofuroxan, the latter being formed via a retro-Boulton-Katritzky rearrangement. The retro rearrangement also occurs on heating the potassium salt of 7-hydroxy-...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 57; no. 18; pp. 2512 - 2515
Main Authors Buncel, Erwin, Chuaqui-Offermanns, Noemi, Norris, Albert R
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 15.09.1979
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Summary:The demethylation of 7-methoxy-4-nitrobenzofuroxan by aqueous KOH gives rise to 7-hydroxy-4-nitrobenzofuroxan as well as 5-hydroxy-4-nitrobenzofuroxan, the latter being formed via a retro-Boulton-Katritzky rearrangement. The retro rearrangement also occurs on heating the potassium salt of 7-hydroxy-4-nitrobenzofuroxan in the solid state. In basic aqueous solution 5-hydroxy-4-nitrobenzofuroxan undergoes the normal Boulton-Katritzky rearrangement to yield 7-hydroxy-4-nitrobenzofuroxan. These processes are rationalized on the basis of a balance between electrostatic and steric interactions in the reactants and the products of rearrangement.
ISSN:0008-4042
1480-3291
DOI:10.1139/v79-400