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Practical synthesis of gem-difluorides from cyclohexanone: Synthesis of gem-bistrifluoroacetates and their reactions with fluoride nucleophiles |
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| Authors: | Masahiro Tojo Shinsuke Fukuoka |
| Affiliation: | a Department of Chemistry, Graduate School of Science, Osaka City University, Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan b Chemistry and Chemical Process Laboratory, Asahi KASEI Chemicals Corporation, 2767-11 Niihama, Kojima-Shionasu, Kurashiki, Okayama 711-8510, Japan c New Business Development, Asahi KASEI Corporation, 1-105 Kanda Jinbocho, Chiyoda-ku, Tokyo 101-8101 Japan |
| Abstract: | Formation of ketone acylals bearing trihaloacetoxy groups and their nucleophilic geminal disubstitution by fluoride ions were investigated. Cyclohexanone reacted with trifluoroacetic anhydride without catalyst to give gem-bistrifluoroacetates via a concerted bimolecular reaction. Treatment with hydrogen fluoride under mild conditions efficiently yielded the corresponding gem-difluorides. In this reaction process, trifluoroacetic acid was recovered and converted to trifluoroacetic anhydride using P2O5. Since gem-difluorides were derived from ketones, HF and P2O5, this constitutes a practical synthesis of gem-difluorides. |
| Keywords: | Fluorination gem-Difluorides Acylals Bistrifluoroacetates |
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