Abstract
Reaction of 2,6-dimethoxy-1,4-benzoquinone with hydroxylamine yielded 2,6-dimethoxy-4-oximino-2,5-cyclohexadienone-1 (3), as confirmed by spectroscopic analysis, and by independent synthesis from 5-nitro-1,2,3-trimethoxybenzene. Infrared and proton magnetic resonance spectra in solution showed no significant proportion of the tautomeric nitrosophenolic form of 3. When 3 was heated for 3 min at 90–95° in 1.0 N HCl in H218O, the N—OH group was stable, but the keto oxygen underwent complete exchange. Mass spectra of 3, its 18O- and deuterium-substituted derivatives indicated that a major process leading to fragmentation upon electron impact was loss of oxygen from N—OH to form the corresponding quinone imine.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
4 articles.
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