Ring-Opening of 1-CF3-Substituted Epoxy Ethers with Carboxylic, Thiocarboxylic, and Phosphinic Acids in Basic Medium and in Hexafluoro-2-propanol
2002; Wiley; Volume: 2002; Issue: 20 Linguagem: Inglês
10.1002/1099-0690(200210)2002
ISSN1434-193X
AutoresJernej Iskra, Danièle Bonnet‐Delpon, Jean‐Pierre Bégué,
Tópico(s)Inorganic Fluorides and Related Compounds
ResumoEuropean Journal of Organic ChemistryVolume 2002, Issue 20 p. 3402-3410 Full Paper Ring-Opening of 1-CF3-Substituted Epoxy Ethers with Carboxylic, Thiocarboxylic, and Phosphinic Acids in Basic Medium and in Hexafluoro-2-propanol Jernej Iskra, Jernej Iskra BIOCIS UPRES-A 8076 CNRS, Faculté de Pharmacie, Université Paris-Sud, Rue J. B. Clément, Châtenay-Malabry, 92296 Cedex, France, Fax: (internat.) + 33-1/46835740Search for more papers by this authorDanièle Bonnet-Delpon, Danièle Bonnet-Delpon [email protected] BIOCIS UPRES-A 8076 CNRS, Faculté de Pharmacie, Université Paris-Sud, Rue J. B. Clément, Châtenay-Malabry, 92296 Cedex, France, Fax: (internat.) + 33-1/46835740Search for more papers by this authorJean-Pierre Bégué, Jean-Pierre Bégué BIOCIS UPRES-A 8076 CNRS, Faculté de Pharmacie, Université Paris-Sud, Rue J. B. Clément, Châtenay-Malabry, 92296 Cedex, France, Fax: (internat.) + 33-1/46835740Search for more papers by this author Jernej Iskra, Jernej Iskra BIOCIS UPRES-A 8076 CNRS, Faculté de Pharmacie, Université Paris-Sud, Rue J. B. Clément, Châtenay-Malabry, 92296 Cedex, France, Fax: (internat.) + 33-1/46835740Search for more papers by this authorDanièle Bonnet-Delpon, Danièle Bonnet-Delpon [email protected] BIOCIS UPRES-A 8076 CNRS, Faculté de Pharmacie, Université Paris-Sud, Rue J. B. Clément, Châtenay-Malabry, 92296 Cedex, France, Fax: (internat.) + 33-1/46835740Search for more papers by this authorJean-Pierre Bégué, Jean-Pierre Bégué BIOCIS UPRES-A 8076 CNRS, Faculté de Pharmacie, Université Paris-Sud, Rue J. B. Clément, Châtenay-Malabry, 92296 Cedex, France, Fax: (internat.) + 33-1/46835740Search for more papers by this author First published: 30 September 2002 https://doi.org/10.1002/1099-0690(200210)2002:20 3.0.CO;2-MCitations: 19Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract Ring-opening of 1-CF3-substituted epoxy ethers with carboxylic acids was achieved in Et3N as solvent, and α-CF3-substituted acyloins and corresponding esters were obtained in good yields. In hexafluoro-2-propanol (HFIP) as solvent, the carboxylic acids acted as nucleophiles, and α-carbonyloxy trifluoromethyl ketones were isolated in good yields. After reduction, CF3-substituted glycols were obtained as monoesters on one or the other hydroxy group. This reaction also allowed the preparation of α-carbonylsulfanyl- and α-phosphoryloxy trifluoromethyl ketones and corresponding alcohols. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002) References 1 J. P. Bégué , D. Bonnet-Delpon , Tetrahedron 1991 , 47 , 3207 −3258 . N. P. Peet, J. P. Burkhart, M. R. Angelastro, E. L. Giroux, S. Mehdi, P. Bey, M. Kolb, B. Neises, D. Schirlin, J. Med. Chem. 1990, 33, 394−407. M. F. Parisi, R. H. Abeles, Biochemistry 1992, 31, 9429−9435. D. V. Patel, K. Rielly-Gauvin, D. E. Ryono, C. A. Free, S. A. Smith, E. W. Petrillo, J. Med. Chem. 1993, 36, 2431−2447. P. Warner, R. C. Green, B. Gomes, A. M. Strimper, J. Med. Chem. 1994, 37, 3090−3099. D. L. Boger, H. Sato, A. E. Lerner, B. J. 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