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class="vector-toc-list"> </ul> </li> <li id="toc-Enolate_Trapping" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Enolate_Trapping"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Enolate Trapping</span> </div> </a> <ul id="toc-Enolate_Trapping-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications_in_Analysis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications_in_Analysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Applications in Analysis</span> </div> </a> <ul id="toc-Applications_in_Analysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Of_metals" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Of_metals"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Of metals</span> </div> </a> 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class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Process of addition of silyl group(s) to compounds</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Silanization" title="Silanization">silanization</a> or <a href="/wiki/Sialylation" class="mw-redirect" title="Sialylation">sialylation</a>.</div> <p><b>Silylation</b> is the introduction of one or more (usually) substituted silyl groups (R<sub>3</sub>Si) to a molecule. Silylations are core methods for production of <a href="/wiki/Organosilicon_chemistry" title="Organosilicon chemistry">organosilicon chemistry</a>. <a href="/wiki/Silanization" title="Silanization">Silanization</a>, while similar to silylation, usually refers to attachment of silyl groups to solids.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Silyl groups are commonly used for: alcohol protection, <a href="/wiki/Enolate" title="Enolate">enolate</a> trapping, <a href="/wiki/Gas_chromatography" title="Gas chromatography">gas chromatography</a>, electron-impact <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a> (EI-MS), and coordinating with metal complexes. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Protection_Chemistry">Protection Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Silylation&action=edit&section=1" title="Edit section: Protection Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Protection">Protection</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Silylation&action=edit&section=2" title="Edit section: Protection"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Silylation is often used to protect alcohols, as well as amines, carboxylic acids, and terminal alkynes. The products after silylation, namely silyl ethers and silyl amines, are resilient toward basic conditions.<sup id="cite_ref-:0_2-0" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Protection is typically done by reacting the functional group with a silyl halide by an <a href="/wiki/SN2_reaction" title="SN2 reaction">SN2 reaction</a> mechanism, typically in the presence of base.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p><span typeof="mw:File"><a href="/wiki/File:Silylation_Protection_Scheme.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Silylation_Protection_Scheme.png/545px-Silylation_Protection_Scheme.png" decoding="async" width="545" height="183" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Silylation_Protection_Scheme.png/818px-Silylation_Protection_Scheme.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Silylation_Protection_Scheme.png/1090px-Silylation_Protection_Scheme.png 2x" data-file-width="1274" data-file-height="428" /></a></span> </p><p>The protection mechanism begins with the base deprotonating the alcohol group. Next, the deprotonated alcohol group attacks the silyl atom of the silyl halide compound. The halide acts as a leaving group and ends up in solution. A workup step follows to remove any excess base within the solution. The overall reaction scheme is as follows: </p> <ol><li><style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">ROH + NEt<sub class="template-chem2-sub">3</sub> → RO<sup class="template-chem2-sup">−</sup> + H−NEt<span class="template-chem2-su"><span>+</span><span>3</span></span></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RO<sup class="template-chem2-sup">−</sup> + Cl−SiMe<sub class="template-chem2-sub">3</sub> → RO−SiMe<sub class="template-chem2-sub">3</sub> + Cl<sup class="template-chem2-sup">−</sup></span></li></ol> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Bis(trimethylsilyl)acetamide.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Bis%28trimethylsilyl%29acetamide.svg/220px-Bis%28trimethylsilyl%29acetamide.svg.png" decoding="async" width="220" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Bis%28trimethylsilyl%29acetamide.svg/330px-Bis%28trimethylsilyl%29acetamide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Bis%28trimethylsilyl%29acetamide.svg/440px-Bis%28trimethylsilyl%29acetamide.svg.png 2x" data-file-width="390" data-file-height="150" /></a><figcaption><a href="/wiki/Bis(trimethylsilyl)acetamide" title="Bis(trimethylsilyl)acetamide">Bis(trimethylsilyl)acetamide</a>, a popular reagent for silylation</figcaption></figure><p>Other silylating agents include <a href="/wiki/Bis(trimethylsilyl)acetamide" title="Bis(trimethylsilyl)acetamide">bis(trimethylsilyl)acetamide</a> (BSA). The reaction of BSA with alcohols gives the corresponding trimethyl<a href="/wiki/Silyl_ether" title="Silyl ether">silyl ether</a>, together with acetamide as a byproduct (Me = CH<sub>3</sub>):<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">2 ROH + MeC(OSiMe<sub class="template-chem2-sub">3</sub>)NSiMe<sub class="template-chem2-sub">3</sub> → MeC(O)NH<sub class="template-chem2-sub">2</sub> + 2 ROSiMe<sub class="template-chem2-sub">3</sub></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Deprotection">Deprotection</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Silylation&action=edit&section=3" title="Edit section: Deprotection"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Due to the strength of the Si-F bond, fluoride salts are commonly used as a deprotecting agent of silyl groups.<sup id="cite_ref-:0_2-1" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The primary fluorous deprotecting agent is <a href="/wiki/Tetra-n-butylammonium_fluoride" title="Tetra-n-butylammonium fluoride">tetra-n-butylammonium fluoride</a> (TBAF), as its aliphatic chains in help incorporate the fluoride ion into organic solvents.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p><span typeof="mw:File"><a href="/wiki/File:Silylation_Deprotection_Scheme.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Silylation_Deprotection_Scheme.png/545px-Silylation_Deprotection_Scheme.png" decoding="async" width="545" height="204" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Silylation_Deprotection_Scheme.png/818px-Silylation_Deprotection_Scheme.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Silylation_Deprotection_Scheme.png/1090px-Silylation_Deprotection_Scheme.png 2x" data-file-width="1220" data-file-height="456" /></a></span> </p><p>Deprotection with a fluoride ion occurs by an S<sub>N</sub>2 mechanism, followed by acidic workup to protonate the resulting alkoxide: </p><p><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">ROSiMe<sub class="template-chem2-sub">3</sub> + NBu<sub class="template-chem2-sub">4</sub>F → RO<sup class="template-chem2-sup">−</sup> + NBu<span class="template-chem2-su"><span>+</span><span>4</span></span> + SiMe<sub class="template-chem2-sub">3</sub>F</span> </p><p>Deprotection of the alcohol can also be done using either Brønsted acids or Lewis acid conditions.<sup id="cite_ref-:2_8-0" class="reference"><a href="#cite_note-:2-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Brønsted acids, like PyBr<sub>3</sub> (pyridinium tribromide), deprotect the alcohol by acting as a proton donor.<sup id="cite_ref-:2_8-1" class="reference"><a href="#cite_note-:2-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Modifying_Silyl_Reactivity">Modifying Silyl Reactivity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Silylation&action=edit&section=4" title="Edit section: Modifying Silyl Reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Silyl.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Silyl.png/220px-Silyl.png" decoding="async" width="220" height="152" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/c/c9/Silyl.png 1.5x" data-file-width="321" data-file-height="222" /></a><figcaption>Common types of alkyl silyl protecting groups</figcaption></figure> <p>Sterically bulkier alkyl substituents tend to decrease the reactivity of the silyl group.<sup id="cite_ref-:02_9-0" class="reference"><a href="#cite_note-:02-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Consequently, bulky substituents increase the silyl group's protective abilities. To add bulkier alkyl silyls, more strenuous conditions are required for alcohol protection. As bulkier groups require more strenuous conditions to add, they also require more strenuous conditions to remove. Additionally, bulkier silyl groups are more selective for the type of alcohols they react with, resulting in a preference for primary alcohols over secondary alcohols. Thus, silyl groups such as TBDMS and TIPS can be used to selectively protect primary alcohols over secondary alcohols.<sup id="cite_ref-:02_9-1" class="reference"><a href="#cite_note-:02-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup>   </p><p>In acidic conditions, alkyl substituents acting as electron withdrawing groups decrease the reaction rate.<sup id="cite_ref-:3_10-0" class="reference"><a href="#cite_note-:3-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> As bulker silyl groups are more likely to be electron withdrawing, it is easier to differentiate between less and more bulky silyl groups.<sup id="cite_ref-:3_10-1" class="reference"><a href="#cite_note-:3-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Therefore, acidic deprotection occurs fastest for less sterically bulky alkyl silyl groups.<sup id="cite_ref-:2_8-2" class="reference"><a href="#cite_note-:2-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> In basic conditions, alkyl substituents acting as electron donating groups decrease reaction rate.<sup id="cite_ref-:3_10-2" class="reference"><a href="#cite_note-:3-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Enolate_Trapping">Enolate Trapping</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Silylation&action=edit&section=5" title="Edit section: Enolate Trapping"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Silylation can also be used to trap reactive compounds for isolation or identification. A common example of this is by trapping reactive enolates into <a href="/wiki/Silyl_enol_ether" title="Silyl enol ether">silyl enol ethers</a>, which represent reactive tautomers of many carbonyl compounds.<sup id="cite_ref-:1_11-0" class="reference"><a href="#cite_note-:1-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> The original enolate can be reformed upon reaction with an organolithium, or other strong base.<sup id="cite_ref-:1_11-1" class="reference"><a href="#cite_note-:1-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p><span typeof="mw:File"><a href="/wiki/File:Enolate_Trapping_by_Silylation.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Enolate_Trapping_by_Silylation.png/800px-Enolate_Trapping_by_Silylation.png" decoding="async" width="800" height="194" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Enolate_Trapping_by_Silylation.png/1200px-Enolate_Trapping_by_Silylation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Enolate_Trapping_by_Silylation.png/1600px-Enolate_Trapping_by_Silylation.png 2x" data-file-width="6200" data-file-height="1500" /></a></span> </p> <div class="mw-heading mw-heading2"><h2 id="Applications_in_Analysis">Applications in Analysis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Silylation&action=edit&section=6" title="Edit section: Applications in Analysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The introduction of a silyl group(s) gives derivatives of enhanced volatility, making the derivatives suitable for analysis by <a href="/wiki/Gas_chromatography" title="Gas chromatography">gas chromatography</a> and electron-impact <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a> (EI-MS). For EI-MS, the silyl derivatives give more favorable diagnostic <a href="/wiki/Fragmentation_pattern" class="mw-redirect" title="Fragmentation pattern">fragmentation patterns</a> of use in structure investigations, or characteristic ions of use in trace analyses employing selected ion monitoring and related techniques.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Of_metals">Of metals</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Silylation&action=edit&section=7" title="Edit section: Of metals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:FpTMS.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/FpTMS.png/170px-FpTMS.png" decoding="async" width="170" height="161" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/FpTMS.png/255px-FpTMS.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d0/FpTMS.png/340px-FpTMS.png 2x" data-file-width="541" data-file-height="512" /></a><figcaption>CpFe(CO)<sub>2</sub>Si(CH<sub>3</sub>)<sub>3</sub>, a trimethylsilyl complex.</figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Transition_metal_silyl_complexes" title="Transition metal silyl complexes">Transition metal silyl complexes</a></div> <p><a href="/wiki/Coordination_complex" title="Coordination complex">Coordination complexes</a> with silyl ligands are well known. An early example is CpFe(CO)<sub>2</sub>Si(CH<sub>3</sub>)<sub>3</sub>, prepared by silylation of CpFe(CO)<sub>2</sub>Na with <a href="/wiki/Trimethylsilyl_chloride" title="Trimethylsilyl chloride">trimethylsilyl chloride</a>. Typical routes include <a href="/wiki/Oxidative_addition" title="Oxidative addition">oxidative addition</a> of Si-H bonds to low-valent metals. Metal silyl complexes are intermediates in <a href="/wiki/Hydrosilation" class="mw-redirect" title="Hydrosilation">hydrosilation</a>, a process used to make <a href="/wiki/Organosilicon_compound" class="mw-redirect" title="Organosilicon compound">organosilicon compounds</a> on both laboratory and commercial scales.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Silylation&action=edit&section=8" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Silyl_ether" title="Silyl ether">Silyl ether</a></li> <li><a href="/wiki/Hydrosilylation" title="Hydrosilylation">Hydrosilylation</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Silylation&action=edit&section=9" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFPape2017" class="citation book cs1">Pape, Peter G. (2017). "Silylating Agents". <i>Kirk-Othmer Encyclopedia of Chemical Technology</i>. pp. <span class="nowrap">1–</span>15. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F0471238961.1909122516011605.a01.pub3">10.1002/0471238961.1909122516011605.a01.pub3</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471238966" title="Special:BookSources/9780471238966"><bdi>9780471238966</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Silylating+Agents&rft.btitle=Kirk-Othmer+Encyclopedia+of+Chemical+Technology&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E15&rft.date=2017&rft_id=info%3Adoi%2F10.1002%2F0471238961.1909122516011605.a01.pub3&rft.isbn=9780471238966&rft.aulast=Pape&rft.aufirst=Peter+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASilylation" class="Z3988"></span></span> </li> <li id="cite_note-:0-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFClaydenGreevesWarren2012" class="citation book cs1">Clayden, Jonathan; Greeves, Nick; Warren, Stuart (2012). <i>Organic chemistry</i> (2nd ed.). Oxford: Oxford university press. pp. <span class="nowrap">549–</span>550. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-927029-3" title="Special:BookSources/978-0-19-927029-3"><bdi>978-0-19-927029-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+chemistry&rft.place=Oxford&rft.pages=%3Cspan+class%3D%22nowrap%22%3E549-%3C%2Fspan%3E550&rft.edition=2nd&rft.pub=Oxford+university+press&rft.date=2012&rft.isbn=978-0-19-927029-3&rft.aulast=Clayden&rft.aufirst=Jonathan&rft.au=Greeves%2C+Nick&rft.au=Warren%2C+Stuart&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASilylation" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPaglianoCampanellaD'UlivoMester2018" class="citation journal cs1">Pagliano, Enea; Campanella, Beatrice; D'Ulivo, Alessandro; Mester, Zoltán (September 2018). <a rel="nofollow" class="external text" href="https://linkinghub.elsevier.com/retrieve/pii/S0003267018304227">"Derivatization chemistries for the determination of inorganic anions and structurally related compounds by gas chromatography - A review"</a>. <i>Analytica Chimica Acta</i>. <b>1025</b>: <span class="nowrap">12–</span>40. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.aca.2018.03.043">10.1016/j.aca.2018.03.043</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Analytica+Chimica+Acta&rft.atitle=Derivatization+chemistries+for+the+determination+of+inorganic+anions+and+structurally+related+compounds+by+gas+chromatography+-+A+review&rft.volume=1025&rft.pages=%3Cspan+class%3D%22nowrap%22%3E12-%3C%2Fspan%3E40&rft.date=2018-09&rft_id=info%3Adoi%2F10.1016%2Fj.aca.2018.03.043&rft.aulast=Pagliano&rft.aufirst=Enea&rft.au=Campanella%2C+Beatrice&rft.au=D%27Ulivo%2C+Alessandro&rft.au=Mester%2C+Zolt%C3%A1n&rft_id=https%3A%2F%2Flinkinghub.elsevier.com%2Fretrieve%2Fpii%2FS0003267018304227&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASilylation" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYoungBuseHeathcock1985" class="citation journal cs1">Young, Steven D.; Buse, Charles T.; Heathcock, Clayton H. 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David (2013-09-02). <a rel="nofollow" class="external text" href="https://www.tandfonline.com/doi/full/10.1080/00397911.2012.717241">"Recent Advances in Silyl Protection of Alcohols"</a>. <i>Synthetic Communications</i>. <b>43</b> (17): <span class="nowrap">2265–</span>2279. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F00397911.2012.717241">10.1080/00397911.2012.717241</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0039-7911">0039-7911</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Synthetic+Communications&rft.atitle=Recent+Advances+in+Silyl+Protection+of+Alcohols&rft.volume=43&rft.issue=17&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2265-%3C%2Fspan%3E2279&rft.date=2013-09-02&rft_id=info%3Adoi%2F10.1080%2F00397911.2012.717241&rft.issn=0039-7911&rft.aulast=Crouch&rft.aufirst=R.+David&rft_id=https%3A%2F%2Fwww.tandfonline.com%2Fdoi%2Ffull%2F10.1080%2F00397911.2012.717241&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASilylation" class="Z3988"></span></span> </li> <li id="cite_note-:02-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-:02_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:02_9-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFClaydenGreevesWarren2012" class="citation book cs1">Clayden, Jonathan; Greeves, Nick; Warren, Stuart (2012). <i>Organic chemistry</i> (2nd ed.). 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Retrieved <span class="nowrap">24 September</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=sigmaaldrich.com&rft.atitle=Silylation+of+Non-Steroidal+Anti-Inflammatory+Drugs&rft.au=Luis-Alberto+Martin&rft.au=Ingrid+Hayenga&rft_id=http%3A%2F%2Fwww.sigmaaldrich.com%2Fanalytical-chromatography%2Fanalytical-reagents%2Fderivatization-reagents%2Fsilylation.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASilylation" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlauJ._M._Halket1993" class="citation book cs1">Blau, Karl; J. M. 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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</span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCoreyBraddock-Wilking1999" class="citation journal cs1">Corey, Joyce Y.; Braddock-Wilking, Janet (1999). 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