89619-11-4Relevant academic research and scientific papers
Catalytic Synthesis of Trifluoromethylated Allenes, Indenes, Chromenes, and Olefins from Propargylic Alcohols in HFIP
No?l, Florent,Vukovi?, Vuk D.,Yi, Jing,Richmond, Edward,Kravljanac, Pavle,Moran, Joseph
, p. 15926 - 15947 (2019/12/25)
A general method to access CF3-substituted allenes from propargylic alcohols under Lewis acid catalysis in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvent is described. By tuning the reaction time and temperature, the obtained allenes rearr
Lewis Acid-Catalyzed Rearrangement of Fluoroalkylated Propargylic Alcohols: An Alternative Approach to β-Fluoroalkyl-α,β-enones
Ramasamy, Manickavasakam,Lin, Hui-Chang,Kuo, Sheng-Chu,Hsieh, Min-Tsang
supporting information, p. 356 - 360 (2019/02/12)
A practical Lewis acid-catalyzed Meyer-Schuster rearrangement of fluoroalkylated propargylic alcohols, leading to a series of β-fluoroalkyl-α,β-enones, is developed. The methodology reported herein features moderate to high yields and high stereoselectivi
HUSY zeolite-promoted reactions of trifluoromethylated propargyl alcohols with arenes: Synthesis of CF3-indenes and DFT study of intermediate carbocations
Nursahedova, Selbi K.,Zerov, Aleksey V.,Boyarskaya, Irina A.,Grinenko, Elena V.,Nenajdenko, Valentine G.,Vasilyev, Aleksander V.
, p. 1215 - 1224 (2019/02/07)
The reaction of CF3-propargyl alcohols [ArCCCH(OH)CF3] with arenes under the action of acidic HUSY zeolite CBV-720 was investigated. It was found that the reaction at 100 °C for 1 h gave rise to 3-aryl-1-CF3-indenes in up
Gold-catalyzed synthesis of β-trifluoromethylated α,β-unsaturated ketones from CF3-substituted propargylic carboxylates and their reactivity in Diels-Alder reactions
Boreux, Arnaud,Lambion, Aubin,Campeau, Dominic,Sanita, Marina,Coronel, Ruben,Riant, Olivier,Gagosz, Fabien
supporting information, p. 5232 - 5239 (2018/06/01)
The synthesis of fluorinated synthetic intermediates has become a field of intense research in organic chemistry. In this article, we report the application of a gold-catalyzed rearrangement to the synthesis of β-trifluoromethylated α,β-unsaturated ketone
Oxidation of α-trifluoromethyl alcohols using a recyclable oxoammonium salt
Kelly, Christopher B.,Mercadante, Michael A.,Hamlin, Trevor A.,Fletcher, Madison H.,Leadbeater, Nicholas E.
, p. 8131 - 8141 (2013/01/15)
A simple, mild method for the oxidation of α-trifluoromethyl alcohols to trifluoromethyl ketones (TFMKs) using the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) is described. Under basic conditions, oxidation proceeds rapidly and affords good to excellent yields of TFMKs, without concomitant formation of the hydrate. The byproduct of the oxidation, 4-acetylamino-2,2,6,6-tetramethyl-1- piperidinyloxy (1c), is easily recovered and can be conveniently reoxidized to regenerate the oxoammonium salt.
Effect of the α-Trifluoromethyl Moiety on the Solvolysis of Allylic Sulfonates
Gassman, Paul G.,Harrington, Clinton K.
, p. 2258 - 2273 (2007/10/02)
A series of allylic sulfonates bearing aryl substituents on the 2-position and/or trifluoromethyl groups on the 1- and/or 3-positions has been studied under solvolytic conditions in 2,2,2-trifluoroethanol.Nonarylated 1,3-di(trifluoromethyl)-substituted allylic sulfonates did not solvolyze in a conventional manner but instead gave products diagnostic of a complex isomerization-cleavage process.Mono(trifluoromethyl)-substituted allylic sulfonates solvolyzed by normal paths to give kH/kCF3 ratios of 2E6 and 4E4 for the substitution at the 1- and 3-positions, respectively.No evidence for 1,3-? interactions was discerned.
