Abstract
2-Perfluoroalkanoylcyclopentane-1,3-diones were synthesized for the first time by acylation of cyclopentane-1,3-dione with perfluorocarboxylic acids in the presence of 1,1′-carbonyldiimidazole or with perfluorocarboxylic anhydrides in the presence of imidazole. 2-Perfluoroalkanoylcyclopentane-1,3-diones were selectively reduced to 2-(1-hydroxyperfluoroalkyl)cyclopentane-1,3-diones by the action of triethylsilane in trifluoroacetic acid in the presence of a catalytic amount of lithium perchlorate. Treatment of the title compounds with oxalyl chloride and subsequent reaction with 2 equiv of primary amine (4-fluoroaniline, 4-fluorobenzylamine, 3,4-difluoroaniline, 3-trifluoromethylbenzylamine) gave the corresponding 3-arylamino-2-perfluoroalkanoylcyclopent-2-en-1-ones.
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Original Russian Text © T.S. Khlebnikova, Yu.A. Piven’, V.G. Isakova, F.A. Lakhvich, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 10, pp. 1283–1288.
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Khlebnikova, T.S., Piven’, Y.A., Isakova, V.G. et al. 2-perfluoroalkanoylcyclopentane-1,3-diones. Synthesis and some transformations. Russ J Org Chem 48, 1277–1282 (2012). https://doi.org/10.1134/S107042801210003X
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DOI: https://doi.org/10.1134/S107042801210003X