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Often silylation is employed to protect OH and NH groups. The derivatives, silyl ethers and silyl amides, are resilient toward many reagents that would attack their precursors. The other main role of silylation is to trap
447:
Mercedes Amat, Sabine Hadida, Swargam
Sathyanarayana, and Joan Bosch "Regioselective Synthesis of 3-Substituted Indoles: 3-Ethylindole" Organic Syntheses 1997, volume 74, page 248.
479:
Moris S. Eisen "Transition-metal silyl complexes" in The
Chemistry of Organic Silicon Compounds. Volume 2 Edited by Zvi Rappoport and Yitzhak Apeloig, 1998, John Wiley & Sons
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Alcohols, carboxylic acids, amines, thiols, and phosphates can be silylated. The process involves the replacement of a proton or an anion with a trialkylsilyl group, typically
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Nina
Gommermann and Paul Knochel "N,N-Dibenzyl-n--amine from Cyclohexanecarbaldehyde, Trimethylsilylacetylene and Dibenzylamine" Organic Syntheses 2007, vol. 84, page 1.
489:
Corey, Joyce Y.; Braddock-Wilking, Janet (1999). "Reactions of
Hydrosilanes with Transition-Metal Complexes: Formation of Stable Transition-Metal Silyl Compounds".
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of use in structure investigations, or characteristic ions of use in trace analyses employing selected ion monitoring and related techniques.
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The introduction of a silyl group(s) gives derivatives of enhanced volatility, making the derivatives suitable for analysis by
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Desilylation is the reverse of silylation: the silyl group is exchanged for a proton. Various fluoride salts (e.g.
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Young, Steven D.; Buse, Charles T.; Heathcock, Clayton H. (1985). "2-Methyl-2-(Trimethylsiloxy)pentan-3-one".
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Silylation has two main uses: manipulation of functional groups and preparation of samples for analysis.
120:)Me is an efficient silylation agent. The reaction of BSA with alcohols gives the corresponding trimethyl
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Identification of
Silylation Artifacts in Derivatization Reactions for Gas Chromatography
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involves similar methods but usually refers to attachment of silyl groups to solids.
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of Si-H bonds to low-valent metals. Metal silyl complexes are intermediates in
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is the introduction of one or more (usually) substituted silyl groups (R
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Si) to a molecule. Silylations are core methods for production of
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with silyl ligands are well known. An early example is CpFe(CO)
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Generally a base is employed to absorb the HCl coproduct.
393:"Silylation of Non-Steroidal Anti-Inflammatory Drugs"
16:Process of addition of silyl group(s) to compounds
124:, together with acetamide as a byproduct (Me = CH
76:), as illustrated by the synthesis of a trimethyl
333:Kirk-Othmer Encyclopedia of Chemical Technology
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341:10.1002/0471238961.1909122516011605.a01.pub3
331:Pape, Peter G. (2017). "Silylating Agents".
420:Handbook of Derivatives for Chromatography
297:on both laboratory and commercial scales.
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62:, a popular reagent for silylation
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417:Blau, Karl; J. M. Halket (1993).
162:Manipulation of functional groups
258:Transition metal silyl complexes
211:) are popular for this purpose.
209:tetra-n-butylammonium fluorides
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110:Bis(trimethylsilyl)acetamide
60:Bis(trimethylsilyl)acetamide
252:, a trimethylsilyl complex.
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285:. Typical routes include
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293:, a process used to make
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378:10.15227/orgsyn.063.0079
19:Not to be confused with
553:Organosilicon compounds
295:organosilicon compounds
283:trimethylsilyl chloride
175:Silylation for analysis
82:trimethylsilyl chloride
39:organosilicon chemistry
263:Coordination complexes
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189:fragmentation patterns
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425:John Wiley & Sons
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223:O → ROH + FSiMe
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533:Desilylation methods
183:and electron-impact
49:Of organic compounds
133:2 ROH + MeC(OSiMe
80:from alcohols and
548:Chemical processes
287:oxidative addition
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181:gas chromatography
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503:10.1021/CR9701086
366:Organic Syntheses
335:. pp. 1–15.
185:mass spectrometry
169:silyl enol ethers
154:Use of silylation
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195:Desilylation
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78:silyl ethers
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43:Silanization
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21:silanization
307:Silyl ether
145:+ 2 ROSiMe
122:silyl ether
25:sialylation
542:Categories
318:References
219:+ F + H
141:→ MeC(O)NH
116:SiNC(OSiMe
112:("BSA", Me
31:Silylation
232:Of metals
205:potassium
511:11848982
301:See also
281:Na with
240:CpFe(CO)
93:ROH + Me
84:(Me = CH
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372:: 79.
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215:ROSiMe
201:sodium
137:)NSiMe
72:(-SiMe
269:Si(CH
244:Si(CH
227:+ OH
101:+ HCl
507:PMID
429:ISBN
404:2023
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