- SILVER (FLUOROSULFONYL)DIFLUOROACETATE - A NEW ROUTE TO FLUOROSULFONYL ESTERS
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New fluorinated esters of the type FSO2CF2C(O)OR and (FSO2CF2C(O)O)2R', (R = CH3, CH3CH2CH2, (CH3)3Si, BrCH2CH2, CH3CH2OC(O)CH2, CH2=CHCH2; R' = CH2, CH2CH2, have been prepared and characterized via the reaction of silver difluoro(fluorosulfonyl)acetate with alkylbromides, alkyliodides, and trimethylsilyl iodide.All new compounds have been characterized by their respective IR/MS/NMR spectra.
- Terjeson, Robin J.,Mohtasham, Javid,Peyton, David H.,Gard, Gary L.
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- Reactive cross-talk between adjacent tension-trapped transition states
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Tension along a polymer chain traps neighboring s-trans/s-trans-1,3- diradicals from the mechanically induced ring opening of gem- difluorocyclopropanes (gDFCs). The diradicals correspond to the transition states of the force-free thermal isomerization reactions of gDFCs, and the tension trapping allows a new disproportionation reaction between two simultaneously trapped diradicals to take place.
- Lenhardt, Jeremy M.,Ogle, James W.,Ong, Mitchell T.,Choe, Robert,Martinez, Todd J.,Craig, Stephen L.
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- Preparation method of trimethylsilyl 2 - (fluorosulfonyl) difluoroacetate
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The invention relates to the technical field of organic synthesis, and provides a preparation method of trimethylsilyl 2 - (fluorosulfonyl) difluoro acetate, which comprises the following steps: S1, adding pyridine in a dry connected three-port flask connected with a constant pressure dropping funnel, nitrogen protection and a tail gas absorption device. S2, 2 - fluorosulfonyl difluoroacetic acid, triethylamine, and control temperature were added. S3, trimethylchlorosilane was added dropwise to control the temperature. S4, after the dropwise addition, heating to reflux, heat preservation reaction. S5. The methanol solution was added to remove the lower layer and distilled to give the product. Through the technical scheme, the problem of low yield of a preparation method in the prior art is solved.
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Paragraph 0024-0044
(2021/10/16)
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- Process for the production of trialkylsilyl(fluorosulfonyl)difluoroacetate
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A process for the production of trialkylsilyl (fluorosulfonyl)difluoroacetate by contacting (fluorosulfonyl)difluoroacetyl fluoride with siloxane. The amount of (fluorosulfonyl)difluoroacetic acid by-product in trialkylsilyl(fluorosulfonyl)difluoroacetate is reduced by contacting said mixture with trialkylsilyl halide.
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Page/Page column 4
(2008/06/13)
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- Trimethylsilyl fluorosulfonyldifluoroacetate (TFDA): A new, highly efficient difluorocarbene reagent
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TFDA is readily prepared from the reaction of fluorosulfonyldifluoroacetic acid with trimethylsilyl chloride, and it is a very effective and efficient source of difluorocarbene for use in addition reactions to alkenes of a broad scope of reactivities. Acid-sensitive substrates may require an additional purification step involving treatment of the distilled TFDA with sufficient Et3N to remove the acid impurity. Other trialkylsilyl fluorosulfonyldifluoroacetates can also be prepared, and they have been found to have reactivities similar to TFDA. The triethyl derivative, TEFDA is more convenient to prepare in a pure state and has similar reactivity to TFDA. Thus, it may prove to be a superior reagent.
- Dolbier Jr., William R.,Tian, Feng,Duan, Jian-Xin,Li, An-Rong,Ait-Mohand, Samia,Bautista, Olivia,Buathong, Saiwan,Baker, J. Marshall,Crawford, Jen,Anselme, Pauline,Cai, Xiao Hong,Modzelewska, Aneta,Koroniak, Henryk,Battiste, Merle A.,Chen, Qing-Yun
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p. 459 - 469
(2007/10/03)
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- Reactivity and regiochemical behavior in the solvolysis reactions of (2,2-difluorocyclopyl)methyl tosylates
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The rate constants for acetolysis of (2,2-difluorocyclopropyl)methyl tosylate, and (2,2-difluoro-3-methylcyclopropyl)methyl tosylate at 92°C and of 1-(2,2-difluoropropyl)ethyl tosylate at 42°C are reported and the rectivities and regiochemistries of ring opening of these systems are discussed and compared with expectations based on computational results. The results are discussed in terms of the use of (2,2-difluorocyclopropyl)methyl systems as mechanistic probes.
- Battiste, Merle A.,Tian, Feng,Baker, John M.,Bautista, Olivia,Villalobos, Janette,Dolbier Jr., William R.
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- A novel and highly efficient synthesis of gem-difluorocyclopropanes
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(Formula presented) A new and highly versatile source of difluorocarbene is reported. Trimethylsilyl fluorosulfonyldifluoroacetate (TFDA) undergoes decomposition in the presence of catalytic fluoride to form difluorocarbene under conditions that allow its addition to relatively electron deficient alkenes in high yield. For example, unprecedented CF2: addition to n-butyl acrylate proceeded in 73percent yield.
- Tian, Feng,Kruger, Virginie,Bautista, Olivia,Duan, Jian-Xin,Li, An-Rong,Dolbier Jr., William R.,Chen, Qing-Yun
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p. 563 - 564
(2007/10/03)
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