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

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

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 1997, Volume: 33, Number: 4, Pages: 471-474 Pages count : 4 DOI: 10.1007/BF02321395

Authors

Samsonov V.A. ¹ , Volodarskii L.V. ¹ , Khisamutdinov G.Kh. ¹

Affiliations

1	(Scopus) Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk 630090, Russian Federation

1,1,4,4-Tetramethoxy-2,3,5,6-tetrahydroximinocyclohexane was obtained by the treatment of trinitrosophloroglucinol 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-benzo[1, 2-c:4,5-c']bis[1.2.5]oxadiazole-1,5-dioxide and 4,4,8,8-tetramethoxy-4H, 8H-benzo[1,2-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-benzo[1,2-c:4,5-c']bis[1.2.5]-dioxazole. Reaction with malonodinitrile gave 4,8-di(dicyanomethylene)-4H,8H-benzo[1,2-c:4,5-c']bis[1.2.5]-oxadiazole which is an analog of known electron acceptors. ©1997 Plenum Publishing Corporation.

Samsonov V.A. , Volodarskii L.V. , Khisamutdinov G.K.
Formation of 1,1,4,4-tetramethoxy-2,3,5,6-tetrahydroximinocyclohexane by the interaction of trinitrosophloroglucinol with hydroxylamine hydrochloride in methanol
Chemistry of Heterocyclic Compounds. 1997. V.33. N4. P.471-474. DOI: 10.1007/BF02321395 Scopus РИНЦ

Published print:

Apr 1, 1997

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