Formation of 1,1,4,4-tetramethoxy-2,3,5,6-tetrahydroximinocyclohexane by the interaction of trinitrosophloroglucinol with hydroxylamine hydrochloride in methanol

1,1,4,4-Tetramethoxy-2,3,5,6-tetrahydroximinocyclohexane was obtained by the treatment of trinitrosoploroglucinol with hydroxylamine hydrochloride in methanol. Oxidation of the product with an alkaline solution of potassium hexacyanoferrrate(III) gave a mixture of the isomers 4,4,8,8-tetramethoxy-4H, 8H-benzo1,2-c:4,5-c']bis1.2.5]oxadiazole-1,7-dioxide.and 4,4,8,8-tetramethoxy-4H, 8H-benzo1,2-c:4,5-c']bis-1.2.5]oxadiazole-1,7-dioxide. Removal of the N-oxide groups from these compounds with triethyl phosphite followed by hydrolysis of the diketal groups gave 4,8-dioxo-4H, 8H-benzo1,2-c:4,5-c']bis1.2.5]-dioxazole. Reaction with malonodinitrile gave 4,8-di(dicyanomethylene)-4H, 8H-benzo1,2-c:4,5-c']bis1.2.5]-oxadiazole which is an analog of known electron acceptors. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Acaemy of Sciences, Novosibirsk 630090. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 549–553, April, 1997.