- Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: Efficient synthesis of 1,1-diaryl-2,2-difluoroethenes
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The cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate (2) with 2 equiv of boronic acids in the presence of catalytic amounts of Pd(OAc)2 and Na2CO3 afforded the mono-coupled products 3 and 5 in high yields. The use of 4 equiv of boronic acid
- Kim, Ju Hee,Choi, Su Jeong,Jeong, In Howa
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supporting information
p. 2470 - 2475
(2014/01/06)
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- Preparation of (2,2-difluoroethenylidene)bis(tributylstannane) and arylation reaction: Efficient approach to 1,1-diaryl-2,2-difluoroethenes
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Reaction of 2,2-difluoro-1-tributylstannylethenyl p-toluenesulfonate (1) with bis(tributyltin) in the presence of 5 mol % Pd(PPh3)4 and 30 equiv LiBr in THF at reflux temperature for 7 h afforded (2,2-difluoroethenylidene)bis(tributylstannane) (2) in a 70% yield. Coupling reaction of 2 with aryl iodides in the presence of 5 mol % Pd(PPh 3)4 and 5 mol % CuI in DMF at 80 °C for 3-4 h provided the coupled products 3 in 59-85% yields.
- Han, Seung Yeon,Lee, Hyo Young,Jeon, Jong Hee,Jeong, In Howa
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supporting information; experimental part
p. 1833 - 1836
(2012/05/04)
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- Kinetics and mechanism of the dehydrohalogenation of Ar2CHCX3 and Ar2CHCHX2 by strong N-bases
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The kinetics and mechanism of the elimination reactions of 1,1,1- trifluoro-, 1,1,1-trichloro-, 1,1,1-tribromo-, 1,1-dichloro- and 1,1-dibromo- 2,2-bis(4-nitrophenyl)ethanes and two strong N-bases: 1,5,7- triazabicyclo[4.4.0]dec-5-ene (TBD) and 7-methyl-1
- Schroeder, Grzegorz,Leska, Boguslawa,Gierczyk, Blazej,Bartosz Rozalski,Brzezinski, Bogumil
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p. 173 - 179
(2007/10/03)
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- CARBANIONS IN E1cB ELIMINATION AND ADDITION REACTIONS
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Visible absorption spectra of the reaction products of di(4-nitrophenyl)methanes derivatives with bases promoted by macrocyclic compounds, are discussed.The kinetic and equilibrium measurements are reported for the reactions: 1,1,1-trifluoro-2,2-di(4-nitr
- Schroeder, G.,Leska, B.,Przybyl, J.
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p. 2063 - 2070
(2007/10/02)
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- KINETICS, MECHANISM AND DEUTERIUM ISOTOPE EFFECT OF THE REACTION OF 1,1,1-TRIFLUORO-2,2-DI(4-NITROPHENYL)ETHANE WITH SODIUM PHENOLATE IN ALCOHOLS. INFLUENCE OF CROWN ETHERS AND CRYPTANDS
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The reaction of 1,1,1-trifluoro-2,2-di(4-nitrophenyl)ethane with sodium phenolate in ethanol, n-propanol, iso-propanol, n-butanol, sec-butanol and t-butanol has been investigated. 1-Fluoro-1-phenoxy-2,2-di(4-nitrophenyl)ethane formed from the intermediate
- Schroeder, Grzegorz
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p. 181 - 192
(2007/10/02)
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- REACTIVITY OF FREE IONS AND ION PAIRS OF ALKOXIDE BASES IN E1cB ELIMINATION REACTIONS. INFLUENCE OF CROWN ETHERS AND CRYPTANDS
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Rate constans and deuterium kinetic isotope effects for free ions and ion pairs of lithium, sodium, potassium ethoxide and propoxidebases for the elimination of HF from 1,1,1-trifluoro-2,2-di(4-nitrophenyl)ethane (Ar2CHCF3) have been calculated.The result
- Schroeder, Grzegorz
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p. 555 - 564
(2007/10/02)
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- KINETICS, ISOTOPE EFFECTS AND MECHANISM OF THE REACTION OF SOME DINITROPHENYLETHANES WITH SODIUM PROPANETHIOLATE IN PROPANOL
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The reaction between Ar2CHCF3, Ar2CHCCl3, Ar2CHCHCl2 (where Ar=O2NC6H4) and sodium propanethiolate in propanol has been investigated.The reaction of Ar2CHCF3 with sodium propanethiolate gave the following alkenes: Ar2C=CF2, Ar2C=CF(SPr) and Ar2C=C(SPr)2,
- Schroeder, Grzegorz
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p. 565 - 576
(2007/10/02)
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- Nucleophilic attack on the carbon-carbon double bond. I. Reaction of primary and secondary amines with 2,2-di(4-nitrophenyl)-1,1-difluoroethene
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The reaction of primary and secondary amines with 2,2-di(4-nitrophenyl)-1,1-difluoroethene (1) in acetonitrile solvent gives first 2,2-di(4-nitrophenyl)-1-fluoro-1-aminoethene (2) and then 2,2-di(4-nitrophenyl)-1,1-difluoro-1-aminoethane (3).With excess a
- Leffek, Kenneth T.,Maciejewska, Urszula
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p. 2274 - 2278
(2007/10/02)
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- The kinetics, isotope effects, and mechanism of the reaction of 2,2-di(4-nitrophenyl)-1,1,1-trifluoroethane with alkoxide bases in alcohol solvents
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The reaction between 2,2-di(4-nitrophenyl)-1,1,1-trifluoroethane and the alkoxide bases O-CH3, O-C2H5, O-nC4H9, O-CH(CH3)2 and O-C(CH3)3 in their corresponding alcohol solvents is a multistep reaction
- Jarczewski, Arnold,Schroeder, Grzegorz,Galezowski, Wlodzimierz,Leffek, Kenneth T.,Maciejewska, Urszula
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p. 576 - 580
(2007/10/02)
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- The influence of crown ethers on the kinetics of E1cB and E2 β-elimination reactions of di(4-nitrophenyl)fluoroethanes with sodium methoxide in methanol
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The addition of crown ethers 1,4,7,10,13 pentaoxacyclopentadecane (15C5)and 1,4,7,10,13,16-hexaoxacyclooctadecane (18C6) in quantities equimolar to the base, to β-elimination reactions of 1,1,1-trifluoro-2,2-di(4-nitrophenyl)ethane and 1-fluoro-2,2,di(4-n
- Leffek, Kenneth T.,Schroeder, Grzegorz
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p. 3077 - 3080
(2007/10/02)
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- The reinvestigation of the kinetics of the reactions of fluorodi(4-nitrophenyl)ethanes with sodium methoxide in methanol
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The procedure previously described for the preparation of 1-fluoro-2,2-di(4-nitrophenyl)ethane actually yields 1,1,2-tri(4-nitrophenyl)ethane.Fluoro-2,2-di(4-nitrophenyl)ethane has been prepared and rate constants, isotope effects, and activation parameters for the β-elimination reaction with methoxide ion in methanol are reported.These parameters indicate a concerted E2 mechanism, with a fairly symmetrical transition state.The subsequent dimerization reaction of the olefin product to yield 1,1,3,3-tetra(4-nitrophenyl)butene-1 is described.The reaction of 1,1,1-trifluoro-2,2-di(4-nitrophenyl)ethane with methoxide ion in methanol has been reinvestigated and the reaction on the first product 1,1-difluoro-2,2-di(4-nitrophenyl)ethylene with excess methoxide, to give di(4-nitrophenyl)ketene dimethylacetal in a multistep reaction, is reported.
- Leffek, Kenneth T.,Schroeder, Grzegorz
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p. 1696 - 1701
(2007/10/02)
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- The reaction between 2,2-di(4-nitrophenyl)1,1,1-trifluoroethane and tert-butoxide ion in tert-butyl alcohol solvent
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The reaction between 2,2-di(4-nitrophenyl)1,1,1-trifluoroethane and excess sodium tert-butoxide in tert-butyl alcohol takes place rapidly to yield first the olefin, by elimination of HF.This is followed by a slower addition of tert-butoxide to the olefin,
- Jarczewski, Arnold,Leffek, Kenneth T.
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p. 1979 - 1982
(2007/10/02)
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