The addition of nitrosyl fluoride to fluoro-olefines

Dyatkin, B. L.; Mochalina, E. P.; Bekker, R. A.; Sterlin, S. R.; Knunyants, I. L.

doi:10.1016/s0040-4020(01)88827-x

Cited by 14 publications

(4 citation statements)

References 5 publications

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“…[10] Various synthetic methods including free radical addition, [11] electrophilic, [12] and nucleophilic [2][3][4][5][6][7][8][9][10] substitution have been employed for the introduction of these groups. Among these methods, nucleophilic substitution of fluoroalkenes, which involves addition followed by b-elimination in the presence of a base, is a well-established strategy.…”

Section: Introductionmentioning

confidence: 99%

Azoles as Reactive Nucleophiles with Cyclic Perfluoroalkenes

Garg

Twamley

Zhang

et al. 2009

Chemistry A European J

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Di- and multiazole-substituted fluorocyclic products (2-13) were readily synthesized in good to high yields. These were synthesized by nucleophilic substitution reactions of perfluorocycloalkenes with azoles (i.e., imidazole, triazole) involving simple reaction procedures. Interestingly, these azoles were later found to be reactive not only with the vinylic, but also with the allylic fluorine atoms. This resulted in the substitution of up to six azoles on the fluorinated rings. Stoichiometry plays a key role in determining the degree of substitution. For comparison, the analogous reactions of N-substituted 1-(trimethylsilyl)-imidazole and 1-(trimethylsilyl)-1,2,4-triazole were also investigated. All of the new compounds were fully characterized by elemental, spectral ((19)F, (1)H, (13)C NMR), and thermal differential scanning calorimetry (DSC) analyses.

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Section: Introductionmentioning

confidence: 99%

Azoles as Reactive Nucleophiles with Cyclic Perfluoroalkenes

Garg

Twamley

Zhang

et al. 2009

Chemistry A European J

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“…The reaction of 1a with CoF 3 at room temperature was completed within 20 min. In the case of ethyl trifluorovinyl ether (1b), 9,11 the reaction with KCoF 4 afforded the corresponding product (2b) in 64% yield, which was better result than the reaction with CoF 3 (entry 1,2). The yield of 2a increased to 70% when the reaction was carried out at a lower temperature (entry 2).…”

mentioning

confidence: 90%

“…to afford CH 3 OCF 2 CF 3 (2a) in 55% yield and slight amount of CH 2 FOCF 2 CF 3 (entry 1). On the other hand, in the case of methyl pentafluoro-1-propenyl ether (1c) 9,12 and methyl heptafluoroisobutenyl ether (1d), 4 the reactions with KCoF 4 resulted in low yields because of cleavage of ether bond, however the reactions with CoF 3 afforded the aimed products in moderate yields (entry 3-6). In the case of the reactions with MnF 3 , AgF 2 , and CeF 4 , the yields were low (entry 3-6).…”

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confidence: 99%

New Synthetic Method of Alkyl Perfluoroalkyl Ethers

2000

Synlett

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“…7 The commercially available nonafluoro-tert-butanol can be obtained by CsF-catalyzed disproportionation of fluoroacetone, 8 by halogen exchange from (F 3 C) 2 (Cl 3 C)COH, 9 or even from the extremely toxic perfluoroisobutene. [10][11][12] More recently, fluoroalkylsilanes such as F 3 CSi(CH 3 ) 3 were successfully used to transfer fluoroalkyl groups to carbonyl compounds, 13,14 anhydrides or activated esters of carboxylic acids, 15 usually in the presence of fluoride as a catalyst.…”

Section: Introductionmentioning

confidence: 99%

The perfluorinated alcohols (F5C6)(F3C)2COH and (F5C6)(F10C5)COH: synthesis, theoretical and acidity studies, spectroscopy and structures in the solid state and the gas phase

Trapp

Scherer

Hayes

et al. 2011

Phys. Chem. Chem. Phys.

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The syntheses of the perfluorinated alcohols (F(5)C(6))(F(3)C)(2)COH (1) and (F(5)C(6))(C(5)F(10))COH (2) are described. Both compounds were prepared in reasonable yields (1: 65%, 2: 85%) by reacting the corresponding ketone with C(6)F(5)MgBr, followed by acidic work-up. The alcohols were characterized by NMR, vibrational spectroscopy, single-crystal X-ray diffraction, acidity measurements and gas-phase electron diffraction. A combination of appropriate 2D NMR experiments allowed the unambiguous assignment of all signals in the (19)F spin systems, of which that of 2 was especially complex. High acidity of the alcohols is indicated by acidity measurements as well as the calculated gas phase acidities. It is also supported by the crystal structure of 2, which exhibits only a single weak intermolecular hydrogen bridge with an O...O distance of 301 pm. This shows the low donor strength of the oxygen atom in the compound, which is partly compensated through formation of two intramolecular CF...H contacts of 220 and 232 pm length to the proton not involved in the hydrogen bridge. The pK(a) values in acetonitrile are 22.2 for 1 and 22.0 for 2; their calculated gas phase acidities are 1367 and 1343 kJ mol(-1) (MP2/TZVPP level).

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The addition of nitrosyl fluoride to fluoro-olefines

Cited by 14 publications

References 5 publications

Azoles as Reactive Nucleophiles with Cyclic Perfluoroalkenes

Azoles as Reactive Nucleophiles with Cyclic Perfluoroalkenes

New Synthetic Method of Alkyl Perfluoroalkyl Ethers

The perfluorinated alcohols (F5C6)(F3C)2COH and (F5C6)(F10C5)COH: synthesis, theoretical and acidity studies, spectroscopy and structures in the solid state and the gas phase

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