| Revision as of 19:10, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,054 edits Saving copy of the {{chembox}} taken from revid 401617134 of page TASF_reagent for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 01:25, 8 January 2025 edit Preimage (talk | contribs)Extended confirmed users1,347 edits added Category:Sulfonium compounds using HotCat |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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| verifiedrevid = 401615926 |
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| verifiedrevid = 470482160 |
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| ImageFile = TASF.png |
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| ImageFile = TASF.png |
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| ImageSize = 200px |
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| ImageSize = 260 |
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| ImageAlt = Skeletal formulas of the TASF reagent |
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| IUPACName = Tris(dimethylamino)sulfonium difluorotrimethylsilicate |
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| ImageFile1 = S(NMe2)3+ (code PILKEA).png |
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| ImageSize1 = 260 |
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| ImageFile2 = SiMe3F2- (code PILKEA).png |
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| PIN = 2-(Dimethylamino)-1,1,3,3-tetramethyldiazathian-2-ium difluorotri(methyl)silanuide |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7971333 |
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| ChemSpiderID = 7971333 |
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| InChI = 1/C6H18N3S.C3H9F2Si/c1-7(2)10(8(3)4)9(5)6;1-6(2,3,4)5/h1-6H3;1-3H3/q+1;-1 |
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| InChI = 1/C6H18N3S.C3H9F2Si/c1-7(2)10(8(3)4)9(5)6;1-6(2,3,4)5/h1-6H3;1-3H3/q+1;-1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = JMGVTLYEFSBAGJ-UHFFFAOYSA-N |
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| StdInChIKey = JMGVTLYEFSBAGJ-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 59218-87-0 --> |
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| PubChem = 9795567 |
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| CASNo = 59218-87-0 |
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| PubChem = 9795567 |
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| SMILES = F(F)(C)(C)C.N((N(C)C)N(C)C)(C)C |
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| SMILES = F(F)(C)(C)C.N((N(C)C)N(C)C)(C)C |
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| Section2 = {{Chembox Properties |
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| C=9|H=27|F=2|Si=1|S=1|N=3 |
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| C=9 | H=27 | F=2 | Si=1 | S=1 | N=3 |
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| MolarMass = 275.48 |
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| MolarMass = 275.48 |
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| Appearance = Colorless solid |
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| Appearance = Colorless solid |
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| MeltingPt = 98-101 °C |
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| MeltingPtC = 98 to 101 |
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The '''TASF reagent''' or '''tris(dimethylamino)sulfonium difluorotrimethylsilicate''' is a ] in ] with ] <sup>+</sup><sup>−</sup>. It is an anhydrous source of ] and is used to cleave ] ]s. Many other fluoride reagents are known, but few are truly anhydrous, because of the extraordinary basicity of "naked" F<sup>−</sup>. In TASF, the fluoride is masked as an adduct with the weak ] trimethylsilylfluoride (FSi(CH<sub>3</sub>)<sub>3</sub>). The ] cation ((CH<sub>3</sub>)<sub>2</sub>N)<sub>3</sub>S<sup>+</sup> is unusually non-electrophilic due to the electron-donating properties of the three (CH<sub>3</sub>)<sub>2</sub>N substituents. |
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This compound is prepared from ]: |
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:3 (CH<sub>3</sub>)<sub>2</sub>NSi(CH<sub>3</sub>)<sub>3</sub> + SF<sub>4</sub> → 2 (CH<sub>3</sub>)<sub>3</sub>SiF + <sup>+</sup><sup>−</sup> |
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The colorless salt precipitates from the reaction solvent, ].<ref>{{OrgSynth | author = W. J. Middleton | title = Tris(dimethylamino)sulfonium difluorotrimethylsilicate | collvol = 7 | collvolpages = 528 | year = 1990 | prep = cv7p0528}}</ref> |
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==Structure== |
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The cation <sup>+</sup> is a ]. The S-N distances are 1.612 and 1.675 pm. The N-S-N angles are 99.6°. The anion is <sup>−</sup>. It is ]al with mutually trans fluorides. The Si-F distances are 176 picometers. The Si-C distances are 188 pm.<ref>{{cite journal |doi=10.1002/hc.520040225|title=Structural studies of tris(dialkylamino) sulfonium (TAS) fluorosilicates|year=1993|last1=Dixon|first1=David A.|last2=Farnham|first2=William B.|last3=Heilemann|first3=W.|last4=Mews|first4=R.|last5=Noltemeyer|first5=M.|journal=Heteroatom Chemistry|volume=4|issue=2–3|pages=287–295}}</ref> |
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==References== |
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<references/> |
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] |
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] |
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