Aci-Quinone Compounds from Eugenoxyacetic Acid and Methyleugenol: Preparation and Reaction

A new aci-quinone compound, 4-(aci-nitro)-2-(methoxy)-5-(3-nitro-2-(nitrooxy)propyl)-cyclohexa-2,5- dienone (2), an analog to 4-(aci-nitro)-2-(carboxymethoxy)-5-(3-nitro-2-(nitrooxy)propyl)-cyclohexa-2,5-dienone (1), was successfully synthesized and fully characterized by spectroscopic methods. The reactions of 1 and 2 with various reagents such as hydroxylamine, acetic anhydride, semicarbazide and thiosemicarbazide were examined. The structure of 11 obtained new compounds was established by IR, 1H NMR, 13C NMR, HMBC and MS spectra. It was shown that the unstable, sensitive aci-quinone structure of compounds 1 and 2 can exist in anhydrous organic solvents such as AcOEt, EtOH but in the presence of water, H+, HO- or at high temperatures, the aci-quinone structure of both 1 and 2 tendentiously transformed into the more stable nitro-phenol form.