- Palladium-catalyzed allylation of 2,2,2-trifluoroethyl phenyl sulfone, a potential 2,2,2-trifluoroethyl pronucleophile
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A palladium-catalyzed allylation reaction of PhSO2CH 2CF3 (2) with a variety of allyl carbonates has been successfully developed for selective 2,2,2-trifluoroethylation under neutral conditions. With this method, the 1-phe
- Zhang, Wei,Zhao, Yanchuan,Ni, Chuanfa,Mathew, Thomas,Hu, Jinbo
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p. 6565 - 6568,4
(2012/12/12)
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- Synthesis and dienophilic reactivity of 1,2-difluorovinylphenylsulfone
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1,2-Difluorovinylphenylsulfone 5 was conveniently prepared in three steps from chlorotrifluoroethylene. Both E and Z isomers of 5 gave excellent yields of [4+2] cycloadducts with cyclopentadiene. The E isomer reacted with high kinetic exo selectivity. 1,2
- De Tollenaere,Ghosez
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p. 17127 - 17138
(2007/10/03)
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- On the preparation and unusual reactivity of a potential difluorodienophile
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Attempts to generate a difluorovinyl sulfone and to react it with cyclopentadiene were hindered by the formation of hydrofluorination products. An α-carbamoyloxy-β,β-difluoroethenyl phenyl sulfone has been prepared in high yield, but reactions with cyclop
- Crowley,Percy,Stansfield
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p. 8233 - 8236
(2007/10/03)
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- NUCLEOPHILIC REACTION AT A VINYL CENTER. XXII. SYNTHESIS AND NUCLEOPHILIC VINYLIC SUBSTITUTION IN E-β-FLUOROVINYL ARYL SULFONES
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The reaction of potassium fluoride with E-β-bromovinyl aryl sulfones in the presence of 18-crown-6-ether leads to a mixture of the sulfones XC6H4SO2CH2CHF2 and E-XC6H4SO2CH=CHF, the ratio of which decreases in the order X=CH3, H, Cl, NO2.The kinetics of n
- Shainyan, B. A.,Mirskova, A. N.
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- NUCLEOPHILIC REACTIONS AT A VINYLIC CENTER. XV. A NEW 1,2-SIGMATROPIC REARRAGMENT IN VINYL ANIONS
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The reactions of a series of β,β-dihalogenovinyl sulfones with potassium fluoride in benzene in the presence of 18-crown-6 ether were investigated.It was found that they undergo isomerization under the indicated conditions to α,β-dihalogenovinyl sulfones,
- Shainyan, B. A.,Mirskova, A. N.,Vitkovskii, V. Yu.
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p. 877 - 884
(2007/10/02)
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- NUCLEOPHILIC REACTIONS AT A VINYL CENTER. XI. EXCHANGE IN β,β-DICHLOROVINYL SULFONES BY FLUORINE AND IODINE
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We studied the reaction of β,β-dichlorovinyl sulfones with potassium fluoride in dimethyl sulfoxide and dimethylformamide, and with sodium iodide in acetone.In the reaction with KF the sulfones RSO2CH2CF3 and RSO2CH3 are formed in a ratio that depends on the amount of water in the organic solvent.Organyl methyl sulfones are not formed in absolute DMSO.A mechanism was proposed for the reaction of β,β-dichlorovinyl sulfones with KF.In the reaction with NaI one chlorine atom is replaced to give the β-chloro-β-iodosulfone.The kinetics of the reactions of ethyl β,β-dichlorovinyl sulfone and ethyl β-chloro-β-iodovinyl sulfone with sodium methoxide in methanol at 0-40 deg C was studied.From a comparison of the activation parameters it follows that in the first step of the reaction of the dichlorovinyl sulfone the chlorine atom cis to the sulfo group is replaced by CH3O-, while in the first step of the reaction of the chloroiodovinyl sulfone the chlorine atom trans to the sulfo group is replaced by CH3O-.The iodine atom is replaced at a rate that is three orders of magnitude slower than that of the chlorine atom.
- Shainyan, B. A.,Mirskova, A. N.
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p. 1022 - 1026
(2007/10/02)
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- Fluoride Ion Elimination-Addition Reactions. Synthesis of 2,2-Difluoroethenyl Phenyl Selenide and 2,2,2-Trifluoroethyl Phenyl Selenide
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2-Chloro-2,2-difluoroethyl phenyl selenide (1) reacts with KF and a catalytic amount of 18-crown-6 to give 2,2-difluoroethenyl phenyl selenide (3) and 2,2,2-trifluoroethyl phenyl selenide (4).The latter is formed by an elimination-addition sequence. 2-Bro
- Feiring, Andrew E.
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p. 1958 - 1961
(2007/10/02)
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