Comparative study of the ring opening of 1-CF3-epoxy ethers mediated by Brönsted acids and hexafluoro-2-propanol |
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Authors: | Jernej Iskra Jean-Pierre Bégué |
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Institution: | BIOCIS UPRES-A 8076 CNRS, Faculté de Pharmacie, Université Paris-Sud, rue J.B. Clément, Châtenay-Malabry 92296 Cedex, France |
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Abstract: | In order to evaluate more deeply the nature of the activation of oxirane ring opening reactions by HFIP, ring opening of both CF3-epoxy ethers 1a (R = Ph) and 1b (R = CH2CH2Ph) with HFIP alone, and with hard (MeOH) or soft (PhSH) nucleophiles in HFIP, were investigated and compared to reactions performed with Brönsted acids. Nucleophilic ring opening reactions in HFIP were facilitated with PhSH and only α-substituted trifluoromethyl ketone 5 was isolated (nucleophilic ring opening), while with MeOH, both processes, nucleophile and electrophile-assisted ring opening were in competition. In the Brönsted acid-catalysed ring opening of 1-CF3-epoxy ethers 1 in HFIP, only the acid-catalysed ring opening process occurred with an inversed regioselectivity. |
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Keywords: | Fluorinated alcohols Hexafluoro-2-propanol Trifluoromethyl-epoxy ethers Trifluoromethyl ketones Oxirane ring-opening Hydrogen bonds Brö nsted acid |
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