- Improved and facile addition reactions of pentafluorosulfanyl bromide
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A solution of SF5Br in CCl3F (0.5-1 M) was utilized to effect the addition of pentafluorosulfanyl bromide (SF5Br) to olefins. The reaction of the SF5Br solution in the presence of triethylborane (0.1 equiv) with an olefin over 20 min at 0 °C gave pentafluorosulfanylated compound 2(a-f) in high yield (Table 2). An efficient route for the preparation of synthetically useful SF5-containing esters is also described.
- Lim, Dong Sung,Ngo, Silvana C.,Lal, Sankar G.,Minnich, Kristen E.,Welch, John T.
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Read Online
- Oxypentafluorosulfate compositions and processes for making them
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Novel compositions are provided containing a compound represented by the formula YOSF5 or ZOSF5, where: (a) Y is: (i) an organic cation other than (Me2N)3S+ or (ii) an inorganic cation, provided that when Y is the inorganic cation, the composition further includes a complexing agent; and (b) Z is C1-20 alkyl, aryl, cycloalkyl, combinations thereof, or analogues thereof containing at least one heteroatom, provided that the compound represented by the formula ZOSF5 is a molecular compound. Processes of making the cationic compounds are disclosed as are processes for using the compositions containing cationic compounds in nucleophilic replacement reactions to prepare the compositions containing molecular compounds including the OSF5 group.
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Page/Page column 4
(2008/06/13)
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- Stable dialkyl ether/poly(hydrogen fluoride) complexes: Dimethyl ether/poly(hydrogen fluoride), a new, convenient, and effective fluorinating agent
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The preparation, 1H, 13C, and 19F NMR structural characterization as well as with DFT-based theoretical calculations of stable dialkyl ether/poly(hydrogen fluoride) complexes are reported. Dimethyl ether/poly(hydrogen fluoride) (DMEPHF), are stable complexes of particular interest and use. The DFT calculations, that are in agreement with NMR data, suggest a cyclic poly(hydrogen fluoride) bridged structure for DMEPHF. The complex, DME-5 HF was found to be a convenient and effective new fluorinating agent with the ease. of workup and applied to several fluorination reactions, such as the hydrofluorination and bromofluorination of alkenes, and fluorination of alcohols giving good to excellent yield with high selectivity. Homologous dialkyl ether/poly(hydrogen fluoride) (R2O/[HF]n R = Et, nPr) systems are also stable and suitable for fluorination reactions.
- Bucsi, Imre,Toeroek, Bela,Marco, Alfonso Iza,Rasul, Golam,Prakash, G. K. Surya,Olah, George A.
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p. 7728 - 7736
(2007/10/03)
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- REACTIONS OF TRIS(DIALKYLAMINO)SULFONIUM TRIMETHYLDIFLUOROSILICATE WITH BROMINE AND IODINE
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Tris(dialkylamino)sulfonium trimethyldifluorosilicates react with bromine and iodine to form tris(dialkylamino)sulfonium bromides (iodides) or tribromides (triiodides), depending on the ratio of the reagents.The structure of tripiperidinosulfonium tribrom
- Markovskii, L. N.,Pashinnik, V. E.,Tovstenko, V. I.,Martynyuk, E. G.,Kramarenko, F. G.,et al.
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p. 1708 - 1712
(2007/10/02)
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- Silver Fluoride Supported on Calcium Fluoride. Improved Fluorination and Halofluorination Reactions
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Silver fluoride dispersed on the surface of calcium fluoride shows improved fluoride nucleophilicity for halogen exchange and addition to alkenes.
- Ando, Takashi,Cork, David G.,Fujita, Mitsue,Kimura, Takahide,Tatsuno, Toshio
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p. 1877 - 1878
(2007/10/02)
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- Electron Transfer Reactions in Organic Chemistry. IX. Acyoxylation and/or Debromodimerization Instead of Electron Transfer in the Reaction between Tris(4-bromophenyl)ammoniumyl and Aliphatic Carboxylates
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The reaction between tris(4-bromophenyl)ammoniumyl tetrafluoroborate and carboxylate ions (acetate, pelargonate and t-butylcyanoacetate), in the form of their hydrogen dicarboxylate salts, was studied in acetonitrile by product and kinetic analysis.Contrary to an earlier proposal, single electron transfer is not observed.Instead, acyloxylation of the aryl group(s) is the preferred reaction mode around room temperature, whereas around 0 deg C, a competing process, debromodimerization of tris(4-bromophenyl)ammoniumyl, takes over.The latter reaction was not observed in dichloromethane.The mechanistic consequences of these findings for other applications of triarylammoniumyls as mediators and catalysts are briefly discussed.Also chloride ion reacted with tris(4-bromophenyl)ammoniumyl to give oxidative substitution products.
- Eberson, Lennart,Larsson, Berit
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p. 210 - 225
(2007/10/02)
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