[2,3,6-trioxypentafulvenes .5(1). Reactions With Primary Amines - Nucleophilic-substitution and Ring Expansion]
(1995) Anales de Quimica — Vol. 91, n° 1-2, p. 32-41 (1995)
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- Abstract
- The reaction between dimethyl 2,3,6-trihydroxypenta-fulvene- 1,4-dicarboxylate and primary alkyl or cycloalkylamines (methylamine, butylamine, cyclooctylamine, cyclohexylamine) affords the corresponding 6-aminopentafulvenes (nucleophilic substitution of the C6 hydroxyl group by the amine) or dimethyl 5-amino-2,3-dihydroxyterephthalates (ring expansion) depending on the reaction conditions. For the two kinds of compounds both a spectroscopic study and a single crystal X-ray analysis have been carried out. Different hydrogen bondings have been observed. Only the substitution products are obtained in the reaction between dimethyl 2,3,6-trihydroxypentafulvene-1,4-dicarboxylate and primary aromatic amines (aniline, 4-sec-butylaniline, p-anisidine). When p-nitroaniline or p-aminobenzonitrile are used the reaction does not progress.
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Victory, P., Alvarezlarena, A., Piniella, JF., Germain, G., Soler, E., & Munoz, M. (1995). [2,3,6-trioxypentafulvenes .5(1). Reactions With Primary Amines - Nucleophilic-substitution and Ring Expansion]. Anales de Quimica, 91(1-2), 32-41. https://hdl.handle.net/2078.5/144791 (Original work published 1995)