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Daniele Bonnetdelpon - One of the best experts on this subject based on the ideXlab platform.
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self promoted nucleophilic addition of Hexafluoro 2 Propanol to vinyl ethers
Advanced Synthesis & Catalysis, 2006Co-Authors: Andrea Di Salvo, Marc David, Benoit Crousse, Daniele BonnetdelponAbstract:In spite of its low nucleophilicity, Hexafluoro-2-Propanol easily adds to vinyl ethers, without catalyst, to afford a range of Hexafluoroisopropyloxy acetals. This addition reaction also occurred in the presence of a competitive, more nucleophilic alcohol. Kinetic studies showed the importance of hydrogen bond parameters in the rate and course of the reaction.
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urea hydrogen peroxide Hexafluoro 2 Propanol an efficient system for a catalytic epoxidation reaction without a metal
European Journal of Organic Chemistry, 2002Co-Authors: Julien Legros, Benoit Crousse, Daniele Bonnetdelpon, Jeanpierre BegueAbstract:Hexafluoro-2-Propanol (HFIP) exhibits a unique ability to release and activate H2O2 from the urea-hydrogen peroxide adduct (UHP). This UHP/HFIP system was investigated in epoxidation of olefins, using various fluoroketones as catalysts. With reactive olefins, no catalyst was required. With monosubstituted olefins, epoxides were obtained in high yields by using catalytic amounts (3−5%) of perfluorodecan-2-one. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
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ring opening of 1 cf3 substituted epoxy ethers with carboxylic thiocarboxylic and phosphinic acids in basic medium and in Hexafluoro 2 Propanol
European Journal of Organic Chemistry, 2002Co-Authors: Jernej Iskra, Daniele Bonnetdelpon, Jeanpierre BegueAbstract: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)
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methyltrioxorhenium catalysed epoxidation of alkenes enhancement of reactivity in Hexafluoro 2 Propanol
Tetrahedron Letters, 2002Co-Authors: Jernej Iskra, Daniele Bonnetdelpon, Jeanpierre BegueAbstract:Abstract Methyltrioxorhenium-catalysed epoxidation of alkenes with hydrogen peroxide can be improved by using Hexafluoro-2-Propanol as a solvent. Quantitative conversions of cyclic and terminal olefins can be obtained with only 30% H 2 O 2 and 0.1 mol% of catalyst.
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1 trifluoromethyl epoxy ethers effect of Hexafluoro 2 Propanol on reactions with secondary aromatic amines synthesis of 3 trifluoromethyl indole derivatives
Journal of Organic Chemistry, 2001Co-Authors: Isabelle Rodrigues, Daniele Bonnetdelpon, Jeanpierre BegueAbstract:Trifluoromethyl epoxy ethers 1 and 2 reacted with aromatic amines in Hexafluoro-2-Propanol at room temperature providing trifluoromethyl indolinols 3 and 4 in excellent isolated yields. 3-Trifluoromethyl indoles 9 and 10 could be prepared by treatment of indolinols with SOCl2.
Jeanpierre Begue - One of the best experts on this subject based on the ideXlab platform.
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urea hydrogen peroxide Hexafluoro 2 Propanol an efficient system for a catalytic epoxidation reaction without a metal
European Journal of Organic Chemistry, 2002Co-Authors: Julien Legros, Benoit Crousse, Daniele Bonnetdelpon, Jeanpierre BegueAbstract:Hexafluoro-2-Propanol (HFIP) exhibits a unique ability to release and activate H2O2 from the urea-hydrogen peroxide adduct (UHP). This UHP/HFIP system was investigated in epoxidation of olefins, using various fluoroketones as catalysts. With reactive olefins, no catalyst was required. With monosubstituted olefins, epoxides were obtained in high yields by using catalytic amounts (3−5%) of perfluorodecan-2-one. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
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ring opening of 1 cf3 substituted epoxy ethers with carboxylic thiocarboxylic and phosphinic acids in basic medium and in Hexafluoro 2 Propanol
European Journal of Organic Chemistry, 2002Co-Authors: Jernej Iskra, Daniele Bonnetdelpon, Jeanpierre BegueAbstract: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)
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methyltrioxorhenium catalysed epoxidation of alkenes enhancement of reactivity in Hexafluoro 2 Propanol
Tetrahedron Letters, 2002Co-Authors: Jernej Iskra, Daniele Bonnetdelpon, Jeanpierre BegueAbstract:Abstract Methyltrioxorhenium-catalysed epoxidation of alkenes with hydrogen peroxide can be improved by using Hexafluoro-2-Propanol as a solvent. Quantitative conversions of cyclic and terminal olefins can be obtained with only 30% H 2 O 2 and 0.1 mol% of catalyst.
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1 trifluoromethyl epoxy ethers effect of Hexafluoro 2 Propanol on reactions with secondary aromatic amines synthesis of 3 trifluoromethyl indole derivatives
Journal of Organic Chemistry, 2001Co-Authors: Isabelle Rodrigues, Daniele Bonnetdelpon, Jeanpierre BegueAbstract:Trifluoromethyl epoxy ethers 1 and 2 reacted with aromatic amines in Hexafluoro-2-Propanol at room temperature providing trifluoromethyl indolinols 3 and 4 in excellent isolated yields. 3-Trifluoromethyl indoles 9 and 10 could be prepared by treatment of indolinols with SOCl2.
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role of Hexafluoro 2 Propanol in selective oxidation of sulfide to sulfoxide efficient preparation of glycosyl sulfoxides
European Journal of Organic Chemistry, 1998Co-Authors: K S Ravikumar, Jeanpierre Begue, Yongmin Zhang, Daniele BonnetdelponAbstract:Aqueous 30% H2O2 in Hexafluoro-2-Propanol (HFIP) is described as a facile, selective and efficient oxidant for the conversion of sulfides to sulfoxides under neutral conditions. The nitrogen center of the pyridine molecule and the carbon–carbon double bond are shown to not be affected by the reagent system used. The oxidation of glycosyl sulfides to glycosyl sulfoxides was achieved in very high yield at room temperature.
J T Gerig - One of the best experts on this subject based on the ideXlab platform.
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examination of interactions of Hexafluoro 2 Propanol with trp cage in Hexafluoro 2 Propanol water by md simulations and intermolecular nuclear overhauser effects
Journal of Physical Chemistry B, 2020Co-Authors: J T GerigAbstract:All-atom molecular dynamic simulations of the peptide Trp-cage in 30% Hexafluoro-2-Propanol– water (V/V) at 278 K have been carried out with the goal of exploring peptide hydrogen-solvent fluorine ...
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interactions of Hexafluoro 2 Propanol with the trp cage peptide
Biochemistry, 2006Co-Authors: Chiradip Chatterjee, J T GerigAbstract:Fluoro alcohols present in aqueous solutions can alter the dominant conformations of peptides and proteins. The origins of these effects likely are related to the details of solute−fluoro alcohol interactions. Preferential interaction of the fluoro alcohol component of a fluoro alcohol−water mixture with peptide solutes has been demonstrated by several experimental approaches. In the present work, we have used 1H{19F} intermolecular NOE experiments to examine interactions of Hexafluoro-2-Propanol in a 30% fluoro alcohol−50 mM phosphate buffer solvent mixture with the “Trp-cage” peptide (NLY IQW LKD GGP SSG RPP PS). The results show that the peptide is selectively solvated by Hexafluoro-2-Propanol to the extent that the fluoro alcohol concentration near the peptide may be 3 to 4 times higher than the nominal concentration of fluoro alcohol in the bulk sample. The observed NOEs indicate that peptide−fluoro alcohol interactions persist for times of the order of 1 ns at 5 °C. As the sample temperature is incr...
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structure and solvation of melittin in 1 1 1 3 3 3 Hexafluoro 2 Propanol water
Biophysical Journal, 2004Co-Authors: J T GerigAbstract:Fluorinated alcohols can induce peptides and proteins to take up helical conformations. Nuclear Overhauser effect (NOE) spectroscopy experiments and analysis of CαH proton chemical shifts show that the conformation of melittin in 35% Hexafluoro-2-Propanol/water is α-helical from residues Ile-2 to Val-8 and from Leu-13 to Gln-25. As has been found in other solvent systems, the two helical regions are not colinear; the interhelix angle (73 ± 15°) in 35% 1,1,1,3,3,3-Hexafluoro-2-Propanol/water is smaller than the angle found in other fluoroalcohol-water mixtures or in the crystal. Intermolecular 1H{19F} and 1H{1H} nuclear Overhauser effects were used to explore interaction of solvent components with melittin dissolved in this solvent mixture. The NOEs observed indicate that fluoroalcohol and water molecules are both tightly bound to the peptide in the vicinity of the interhelix bend. For the remainder of the molecule, solute-solvent NOEs are consistent with preferential solvation of the peptide by the fluoroalcohol component of the solvent mixture.
Jin Qu - One of the best experts on this subject based on the ideXlab platform.
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Simple and Efficient Synthesis of Tetrahydro-β-carbolines via the Pictet—Spengler Reaction in 1,1,1,3,3,3-Hexafluoro-2-Propanol (HFIP).
ChemInform, 2015Co-Authors: Li-na Wang, Su-li Shen, Jin QuAbstract:Hexafluoro-2-Propanol acts as both the solvent and the catalyst to promote the title reaction between tryptamine derivatives [(I) or (VI)] or tyramine derivative (IX), resp., and aldehydes (II) or ketones (IV), respectively.
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intramolecular etherification and polyene cyclization of π activated alcohols promoted by hot water
Journal of Organic Chemistry, 2015Co-Authors: Fengzhi Zhang, Yan Tian, Guoxing Li, Jin QuAbstract:Hot water, acting as a mildly acidic catalyst, efficiently promoted intramolecular direct nucleophilic substitution reactions of unsaturated alcohols with heteroatom or carbon nucleophiles. In a mixed solvent of water and 1,1,1,3,3,3-Hexafluoro-2-Propanol (HFIP), polyene cyclizations using allylic alcohols as initiators gave the desired cyclized products, and in neat HFIP, a tricyclization reaction gave a tetracyclic product in 51% chemical yield.
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Simple and efficient synthesis of tetrahydro-β-carbolines via the Pictet–Spengler reaction in 1,1,1,3,3,3-Hexafluoro-2-Propanol (HFIP)
RSC Advances, 2014Co-Authors: Li-na Wang, Su-li Shen, Jin QuAbstract:1,1,1,3,3,3-Hexafluoro-2-Propanol (HFIP) can act as both the solvent and the catalyst to promote the Pictet–Spengler reactions between tryptamine derivatives and aldehydes or activated ketones. For most substrates, removing the low boiling point HFIP by distillation directly afforded tetrahydro-β-carbolines in high yields.
Zoon Ha Ryu - One of the best experts on this subject based on the ideXlab platform.
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Communication Additional Solvent Ionizing Power Values for Binary Water- 1,1,1,3,3,3-Hexafluoro-2-Propanol Solvents
2015Co-Authors: Dennis N. Kevill, Zoon Ha RyuAbstract:Abstract: Determinations of the specific rates of solvolysis of 1-adamantyl bromide and 1-adamantyl iodide in 1,1,1,3,3,3-Hexafluoro-2-Propanol-water mixtures, in conjunction with earlier reported values in 80 % ethanol, have led to additional YBr and YI solvent ionizing power values. These new values will be especially important in avoiding multicollinearity when the extended Grunwald-Winstein equation (extended by addition of a term involving solvent nucleophilicity) is used to correlate solvent-induced changes in the specific rates of solvolyses involving a bromide or iodide ion leaving group
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additional solvent ionizing power values for binary water 1 1 1 3 3 3 Hexafluoro 2 Propanol solvents
International Journal of Molecular Sciences, 2006Co-Authors: Dennis N. Kevill, Zoon Ha RyuAbstract:Determinations of the specific rates of solvolysis of 1-adamantyl bromide and 1-adamantyl iodide in 1,1,1,3,3,3-Hexafluoro-2-Propanol-water mixtures, in conjunction withearlier reported values in 80% ethanol, have led to additional YBr and YI solvent ionizingpower values. These new values will be especially important in avoiding multicollinearitywhen the extended Grunwald-Winstein equation (extended by addition of a term involvingsolvent nucleophilicity) is used to correlate solvent-induced changes in the specific rates ofsolvolyses involving a bromide or iodide ion leaving group.