Synthesis of trifluoromethyl alcohols from tert-butoxy-β-(trifluoromethyl)styrenes and trifluoromethylbenzyl ketones under the conditions of the Leuckart–Wallach reaction

Muzalevskiy, Vasiliy M.; Nenajdenko, Valentine G.; Шастин, А. В.; Баленкова, Е. С.; Haufe, Günter

doi:10.1016/j.jfluchem.2008.06.014

Cited by 13 publications

(1 citation statement)

References 27 publications

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“…colorless oil; yield 90% (1.0 g); 1 H NMR (400 MHz, CDCl 3 ) δ 7.35 (d, J = 8.4 Hz, 2H), 7.15 (d, J = 8.4 Hz, 2H), 3.99 (s, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 188.9 (q, J = 35.0 Hz), 134.4, 131.3, 129.5, 129.0, 116.0 (q, J = 290.6 Hz), 42.6; 19 F NMR (376 MHz, CDCl 3 ) δ −78.8; HRMS (ESI) m / z calcd for C 9 H 6 ClF 3 O 222.0060, found 222.0059. These spectroscopic data correspond to previously reported data …”

Section: Methodssupporting

confidence: 92%

Synthesis of Trifluoromethyl Ketones via Tandem Claisen Condensation and Retro-Claisen C–C Bond-Cleavage Reaction

et al. 2013

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A highly efficient, operationally simple approach to trifluoromethyl ketones has been developed that builds on the use of a tandem process involving Claisen condensation and retro-Claisen C-C bond cleavage reaction. Enolizable alkyl phenyl ketones were found to react readily with ethyl trifuoroacetate under the promotion of NaH to afford trifluoroacetic ester/ketone exchange products, trifluoromethyl ketones, which were quite different from the general Claisen condensation products, β-diketones. This procedure uses readily available starting materials and can be extended to the preparation of perfluoroalkyl ketones in excellent yield.

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Section: Methodssupporting

confidence: 92%