Abstract
The diene condensation of β-nitro and β-bromo-β-nitroacrylates with 2-(2-nitroethenyl)furan as 1,3-diene leads to a mixture of regioisomeric tetrahydrobenzofurans transforming under the reaction conditions into benzofurancarboxylates due to the easy dehydrohalogenation, denitration, and dehydration. In the case of a gem-bromonitroacrylate reaction takes two routes: diene synthesis and alkylation of the furan ring, the latter process prevailing. The structure of products formed was established by spectral methods. The investigation of geometry of 2-(1-methoxycarbonyl-2-nitroethenyl)-5-(2-nitroethenyl)furan by XRD analysis showed that its vinyl fragments have the coplanar chelate-like structure with the cisoid orientation of the CO2Me and NO2 groups. The ester group deviates from the plane of the the carbon-carbon multiple bond.
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Original Russian Text © V.M. Berestovitskaya, N.A. Anisimova, O.N. Kataeva, G.A. Berkova, A. Jager, 2008, published in Zhurnal Obschei Khimii, 2008, Vol. 78, No. 5, pp. 811–819.
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Berestovitskaya, V.M., Anisimova, N.A., Kataeva, O.N. et al. Reaction of alkyl-3-nitro-and-3-bromo-3-nitroacrylates with 2-(2-nitroethenyl)furan. Russ J Gen Chem 78, 954–962 (2008). https://doi.org/10.1134/S1070363208050216
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DOI: https://doi.org/10.1134/S1070363208050216