Interconversion of benzofurazandione monoximes

The preparation of 5-hydroxy-4-nitroso- and 7-hydroxy-4-nitrosobenzofurazan as well as of their 6-chloro and methyl derivatives is described and the oxime structure of these compounds is established. NMR spectra of benzofurazan-4,5-dione-4-monoxime and benzofurazan-4,7-dione-4-monoxime show evidence for an interconversion, in solution, of two monoximes, the 4,5- and 4,7-derivative prevailing in organic solvents and aqueous alkaline media, respectively. Chloro and methyl derivatives of benzofurazan-4,5- and 4,7-dione-4-monoximes show a similar interconversion in organic solvents.