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Reactions of substituted N-(5-nitro-2-furfuryl)anilines

R. Mocelo and J. Kováč

Department of Organic Chemistry, Faculty of Chemistry, University of Havana

 

Abstract: Nitrosation of substituted 7V-(5-nitio-2-furfuryl)anilines gave the corre­sponding N-nitroso derivatives, which in the conditions of Fischer—Hepp rearrangement suffered anomalous denitrosation to chlorides of the starting compounds. Low reactivity of NH group of anilines precluded its acylation, benzoylation, using acetic anhydride and benzoyl chloride, respectively. Azo-coupling with diazonium salts proceeded in position 4 of the benzene ring, in case of more reactive 4-nitrobenzenediazonium chloride even N-diazo derivative was formed.

Full paper in Portable Document Format: 425a665.pdf

 

Chemical Papers 42 (5) 665–675 (1988)

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