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Organosilicon chemistry
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<h2 id="history">History</h2> <p class="note">See also: <a href="/facts/Organometallic_chemistry/bhqFz2P0">Organometallic chemistry</a></p> <p>In 1863, <a href="/facts/Charles_Friedel/NmpjE35F">Charles Friedel</a> and <a href="/facts/James_Crafts/CuTNM5VI">James Crafts</a> made the first organochlorosilane compound.<a class="footnote-ref" id="fnref:1" href="#fn:1"><sup>1</sup></a> The same year, they also described a "polysilicic acid ether" in the preparation of <a href="/facts/Ethanol/3lCLfBSP">ethyl-</a> and methyl-o-silicic acid.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a> Extensive research in the field of organosilicon compounds was pioneered in the beginning of 20th century by <a href="/facts/Frederic_Kipping/yCbBvLC5">Frederic S. Kipping</a>.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> He also had coined the term "silicone" (resembling <i><a href="/facts/Ketone/BqQXpLo4">ketones</a></i>, though this is erroneous)<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a><a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a>: 286 in relation to these materials in 1904. In recognition of Kipping's achievements, the <a href="/facts/Dow_Chemical_Company/tuTEe6tQ">Dow Chemical Company</a> had established an award in the 1960s that is given for significant contributions to the field of silicon chemistry.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> In his works, Kipping was noted for using <a href="/facts/Grignard_reagent/0vkLtPo1">Grignard reagents</a> to make <a href="/facts/Alkyl/vmEk8X4v">alkyl</a>silanes and <a href="/facts/Aryl/M3z7QRXd">aryl</a>silanes and preparing <a href="/facts/Silicone_resin/qPLQwJha">silicone oligomers</a> and polymers for the first time.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> </p><p>In 1945, <a href="/facts/Eugene_G._Rochow/7jXAulwl">Eugene G. Rochow</a> also made a significant contribution to the field of organosilicon chemistry by first describing the <a href="/facts/M%C3%BCller-Rochow_process/wDu3X0bQ">Müller-Rochow process</a>.<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a> </p> <h2 id="occurrence-and-applications">Occurrence and applications</h2> <p>Organosilicon compounds are widely encountered in commercial products. Most common are antifoamers, <a href="/facts/Caulk/LgQruKW3">caulks</a> (sealant), adhesives, and coatings made from <a href="/facts/Silicone/4AX8YA5m">silicones</a>. Other important uses include agricultural and plant control <a href="/facts/Adjuvant/jnRqeBnG">adjuvants</a> commonly used in conjunction with <a href="/facts/Herbicide/FN93bvrk">herbicides</a> and <a href="/facts/Fungicide/c1twQBYo">fungicides</a>.<a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a> </p> <h3>Biology and medicine</h3> <p>Carbon–silicon bonds are absent in <a href="/facts/Biochemistry/fa2pWEBp">biology</a>, however enzymes have been used to artificially create carbon-silicon bonds in living microbes.<a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a><a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a><a class="footnote-ref" id="fnref:12" href="#fn:12"><sup>12</sup></a> <a href="/facts/Silicate/7NdthSRM">Silicates</a>, on the other hand, have known existence in <a href="/facts/Diatom/x2oEcP1P">diatoms</a>.<a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a> <a href="/facts/Silafluofen/kswInJmk">Silafluofen</a> is an organosilicon compound that functions as a <a href="/facts/Pyrethroid/Lf1N0STQ">pyrethroid</a> <a href="/facts/Insecticide/1xYL3MSD">insecticide</a>. Several organosilicon compounds have been investigated as pharmaceuticals.<a class="footnote-ref" id="fnref:14" href="#fn:14"><sup>14</sup></a><a class="footnote-ref" id="fnref:15" href="#fn:15"><sup>15</sup></a> </p> <h2 id="bonding">Bonding</h2> Electronegativities Relevant to Organosilicon Chemistry<table><tbody><tr><th>C</th><th>Si</th><th>H</th><th>O</th></tr><tr><td>2.5</td><td>1.8</td><td>2.1</td><td>3.4</td></tr></tbody></table> Properties Relevant to Organosilicon Chemistry<table><tbody><tr><th>Bond</th><th>Bond length (pm)</th><th>Approx. bond strength (kJ/mol)</th></tr><tr><td>C-C</td><td>154</td><td>334</td></tr><tr><td>Si-Si</td><td>234</td><td>196</td></tr><tr><td>C-Si</td><td>186</td><td>314</td></tr><tr><td>C-H</td><td>110</td><td>414</td></tr><tr><td>Si-H</td><td>146</td><td>314</td></tr><tr><td>C-O</td><td>145</td><td>355</td></tr><tr><td>Si-O</td><td>159</td><td>460</td></tr></tbody></table> Dissociation energies of bonds to silicon<a class="footnote-ref" id="fnref:16" href="#fn:16"><sup>16</sup></a><table><tbody><tr><th>Bond</th><th>Energy (kJ/mol)</th></tr><tr><td>Si–Si</td><td>327(10)</td></tr><tr><td>Si–Br</td><td>343(50)</td></tr><tr><td>Si–C</td><td>435(21)</td></tr><tr><td>Si–Cl</td><td>456(42)</td></tr><tr><td>Si–F</td><td>540(13)</td></tr><tr><td>Si–H</td><td>298.49(46)</td></tr><tr><td>Si–I</td><td>339(84)</td></tr><tr><td>Si–N</td><td>439(38)</td></tr><tr><td>Si–O</td><td>798(8)</td></tr><tr><td>Si–S</td><td>619(13)</td></tr><tr><td>Si–Se</td><td>531(25)</td></tr><tr><td>H3Si–SiH3</td><td>339(17)</td></tr><tr><td><a href="/facts/Methyl/fkM97EMD">Me</a>3Si–SiMe3</td><td>339</td></tr><tr><td><a href="/facts/Aryl/M3z7QRXd">Ar</a>3Si–SiAr3</td><td>368(31)</td></tr><tr><td>Si–Te</td><td>506(38)</td></tr></tbody></table> <p>In the great majority of organosilicon compounds, Si is <a href="/facts/Tetravalent/ck7cHByj">tetravalent</a> with <a href="/facts/Tetrahedral_molecular_geometry/583AL1sP">tetrahedral molecular geometry</a>. Compared to carbon–carbon bonds, carbon–silicon bonds are longer and weaker.<a class="footnote-ref" id="fnref:17" href="#fn:17"><sup>17</sup></a><a class="footnote-ref" id="fnref:18" href="#fn:18"><sup>18</sup></a> </p><p>The C–Si bond is somewhat polarised towards carbon due to carbon's greater <a href="/facts/Electronegativity/H7Vq7Uah">electronegativity</a> (C 2.55 vs Si 1.90), and single bonds from Si to electronegative elements are very strong.<a class="footnote-ref" id="fnref:19" href="#fn:19"><sup>19</sup></a> Silicon is thus susceptible to nucleophilic attack by O−, Cl−, or F−; the energy of an <a href="/facts/Silicon%E2%80%93oxygen_bond/3smJyhVQ">Si–O bond</a> in particular is strikingly high. This feature is exploited in many reactions such as the <a href="/facts/Sakurai_reaction/hUSHBA65">Sakurai reaction</a>, the <a href="/facts/Brook_rearrangement/FcKGXDxF">Brook rearrangement</a>, the <a href="/facts/Fleming%E2%80%93Tamao_oxidation/lBUIFh8e">Fleming–Tamao oxidation</a>, and the <a href="/facts/Peterson_olefination/vSnD9JIm">Peterson olefination</a>.<a class="footnote-ref" id="fnref:20" href="#fn:20"><sup>20</sup></a> </p><p>The Si–C bond (1.89 Å) is significantly longer than a typical C–C bond (1.54 Å), suggesting that silyl substitutents have less steric demand than their organyl analogues. When geometry allows, <a href="/facts/Negative_hyperconjugation_in_silicon/EaPmn2Uq">silicon exhibits negative hyperconjugation</a>, reversing the usual polarization on neighboring atoms. </p> <h2 id="preparation">Preparation</h2> <p>The first organosilicon compound, tetraethylsilane, was prepared by <a href="/facts/Charles_Friedel/NmpjE35F">Charles Friedel</a> and <a href="/facts/James_Crafts/CuTNM5VI">James Crafts</a> in 1863 by reaction of <a href="/facts/Tetrachlorosilane/MXnhxpVK">tetrachlorosilane</a> with <a href="/facts/Diethylzinc/b7eYFsy3">diethylzinc</a>. </p><p>The bulk of organosilicon compounds derive from organosilicon chlorides (CH3)4-xSiClx. These chlorides are produced by the "<a href="/facts/Direct_process/wDu3X0bQ">Direct process</a>", which entails the reaction of <a href="/facts/Methyl_chloride/DvmeEgDS">methyl chloride</a> with a silicon-copper alloy. The main and most sought-after product is <a href="/facts/Dimethyldichlorosilane/V3rMdG5t">dimethyldichlorosilane</a>: </p> 2 CH3Cl + Si → (CH3)2SiCl2 <p>A variety of other products are obtained, including <a href="/facts/Trimethylsilyl_chloride/CKlvuSgR">trimethylsilyl chloride</a> and <a href="/facts/Methyltrichlorosilane/4F74TXe6">methyltrichlorosilane</a>. About 1 million tons of organosilicon compounds are prepared annually by this route. The method can also be used for phenyl chlorosilanes.<a class="footnote-ref" id="fnref:21" href="#fn:21"><sup>21</sup></a> </p> <h3>Hydrosilylation</h3> <p class="note">Main article: <a href="/facts/Hydrosilylation/dPqlRe0t">Hydrosilylation</a></p> <p>Another major method for the formation of Si-C bonds is hydrosilylation (also called hydrosilation).<a class="footnote-ref" id="fnref:22" href="#fn:22"><sup>22</sup></a> In this process, compounds with Si-H bonds (<a href="/facts/Hydrosilane/bIkgTqf1">hydrosilanes</a>) are added to unsaturated substrates. Commercially, the main substrates are <a href="/facts/Alkene/RtYcS6kU">alkenes</a>. Other unsaturated functional groups — <a href="/facts/Alkyne/VHI4N5Wo">alkynes</a>, <a href="/facts/Imine/yK72z07j">imines</a>, <a href="/facts/Ketone/BqQXpLo4">ketones</a>, and <a href="/facts/Aldehyde/xSIRkW03">aldehydes</a> — also participate, but these reactions are of little economic value.<a class="footnote-ref" id="fnref:23" href="#fn:23"><sup>23</sup></a> </p> <p>Hydrosilylation requires metal catalysts, especially those based on <a href="/facts/Platinum_group_metal/pbDgst54">platinum group metals</a>. </p><p>In the related <a href="/facts/Carbometalation/PPA3WdMv">silylmetalation</a>, a metal replaces the hydrogen atom. </p> <h2 id="functional-groups">Functional groups</h2> <p>Silicon is a component of many functional groups. Most of these are analogous to organic compounds. The overarching exception is the rarity of multiple bonds to silicon, as reflected in the <a href="/facts/Double_bond_rule/kxtnRvH8">double bond rule</a>. </p> <h3>Silanols, siloxides, and siloxanes</h3> <p><a href="/facts/Silanol/3f58wE1l">Silanols</a> are analogues of alcohols. They are generally prepared by hydrolysis of silyl chlorides:<a class="footnote-ref" id="fnref:24" href="#fn:24"><sup>24</sup></a> </p> R3SiCl + <a href="/facts/Water/0lkXnJPK">H2O</a> → R3SiOH + HCl <p>Less frequently silanols are prepared by oxidation of silyl hydrides, a reaction that uses a metal catalyst: </p> 2 R3SiH + O2 → 2 R3SiOH <p>Many silanols have been isolated including <a href="/facts/Trimethylsilanol/N9czlqxt">(CH3)3SiOH</a> and (C6H5)3SiOH. They are about 500x more acidic than the corresponding alcohols. <a href="/facts/Siloxide/mDbVbTBh">Siloxides</a> are the deprotonated derivatives of silanols:<a class="footnote-ref" id="fnref:25" href="#fn:25"><sup>25</sup></a> </p> R3SiOH + NaOH → R3SiONa + <a href="/facts/Water/0lkXnJPK">H2O</a> <p>Silanols tend to dehydrate to give <a href="/facts/Siloxane/6fbEIal7">siloxanes</a>: </p> 2 R3SiOH → R3Si-O-SiR3 + <a href="/facts/Water/0lkXnJPK">H2O</a> <p>Polymers with repeating siloxane linkages are called <a href="/facts/Silicone/4AX8YA5m">silicones</a>. Compounds with an Si=O double bond called <a href="/facts/Silanone/SI1h9e6q">silanones</a> are extremely unstable. </p> <h3>Silyl ethers</h3> <p><a href="/facts/Silyl_ether/k6y8Th9E">Silyl ethers</a> have the connectivity Si-O-C. They are typically prepared by the reaction of alcohols with silyl chlorides: </p> (CH3)3SiCl + ROH → (CH3)3Si-O-R + HCl <p>Silyl ethers are extensively used as <a href="/facts/Protective_group/f92hVwHl">protective groups</a> for <a href="/facts/Alcohol_(chemistry)/Y0SCTDkh">alcohols</a>. </p><p>Exploiting the strength of the Si-F bond, fluoride sources such as <a href="/facts/Tetra-n-butylammonium_fluoride/RN8vHQsy">tetra-n-butylammonium fluoride</a> (TBAF) are used in deprotection of silyl ethers: </p> (CH3)3Si-O-R + F− + <a href="/facts/Water/0lkXnJPK">H2O</a> → (CH3)3Si-F + H-O-R + OH− <h3>Silyl chlorides</h3> <p class="note">Main article: <a href="/facts/Chlorosilane/GnV3kQ21">Chlorosilane</a></p> <p>Organosilyl chlorides are important commodity chemicals. They are mainly used to produce <a href="/facts/Silicone/4AX8YA5m">silicone</a> polymers as described above. Especially important silyl chlorides <a href="/facts/Dimethyldichlorosilane/V3rMdG5t">dimethyldichlorosilane</a> (Me2SiCl2), <a href="/facts/Methyltrichlorosilane/4F74TXe6">methyltrichlorosilane</a> (MeSiCl3), and <a href="/facts/Trimethylsilyl_chloride/CKlvuSgR">trimethylsilyl chloride</a> (Me3SiCl) are all produced by <a href="/facts/Direct_process/wDu3X0bQ">direct process</a>. More specialized derivatives that find commercial applications include dichloromethylphenylsilane, trichloro(chloromethyl)silane, trichloro(dichlorophenyl)silane, trichloroethylsilane, and phenyltrichlorosilane. </p><p>Although proportionately a minor outlet, organosilicon compounds are widely used in <a href="/facts/Organic_synthesis/aprl6Iq7">organic synthesis</a>. Notably <a href="/facts/Trimethylsilyl_chloride/CKlvuSgR">trimethylsilyl chloride</a> Me3SiCl is the main silylating agent. One classic method called the Flood reaction for the synthesis of this compound class is by heating hexaalkyldisiloxanes R3SiOSiR3 with concentrated <a href="/facts/Sulfuric_acid/Wom6fymJ">sulfuric acid</a> and a sodium <a href="/facts/Halide/ujYu8kGD">halide</a>.<a class="footnote-ref" id="fnref:26" href="#fn:26"><sup>26</sup></a> </p> <h3>Silyl hydrides</h3> <p class="note">Main article: <a href="/facts/Hydrosilane/bIkgTqf1">Hydrosilane</a></p> <p>The silicon to hydrogen bond is longer than the C–H bond (148 compared to 105 pm) and weaker (299 compared to 338 kJ/mol). Hydrogen is more <a href="/facts/Electronegativity/H7Vq7Uah">electronegative</a> than silicon hence the naming convention of silyl <i>hydrides</i>. Commonly the presence of the hydride is not mentioned in the name of the compound. Triethylsilane has the formula Et3SiH. Phenylsilane is PhSiH3. The parent compound SiH4 is called <a href="/facts/Silane/XNevDLgE">silane</a>. </p> <h3>Silenes</h3> <p>Organosilicon compounds, unlike their carbon counterparts, do not have a rich <a href="/facts/Double_bond/qDemMn0c">double bond</a> chemistry.<a class="footnote-ref" id="fnref:27" href="#fn:27"><sup>27</sup></a> Compounds with silene Si=C bonds (also known as alkylidenesilanes) are laboratory curiosities such as the silicon benzene analogue <a href="/facts/Silabenzene/d56I88FT">silabenzene</a>. In 1967, Gusel'nikov and Flowers provided the first evidence for silenes from pyrolysis of <i>dimethylsilacyclobutane</i>.<a class="footnote-ref" id="fnref:28" href="#fn:28"><sup>28</sup></a> The first stable (kinetically shielded) silene was reported in 1981 by Brook.<a class="footnote-ref" id="fnref:29" href="#fn:29"><sup>29</sup></a><a class="footnote-ref" id="fnref:30" href="#fn:30"><sup>30</sup></a> </p><p><a href="/facts/Disilene/yknxER4V">Disilenes</a> have Si=Si double bonds and <a href="/facts/Disilyne/sXkfm1Yg">disilynes</a> are silicon analogues of an alkyne. The first Silyne (with a silicon to carbon triple bond) was reported in 2010.<a class="footnote-ref" id="fnref:31" href="#fn:31"><sup>31</sup></a> </p> <h3>Siloles</h3> <p>Siloles, also called silacyclopentadienes, are members of a larger class of compounds called <a href="/facts/Metallole/g0HKfW40">metalloles</a>. They are the silicon analogs of <a href="/facts/Cyclopentadiene/S66eVYvh">cyclopentadienes</a> and are of current academic interest due to their <a href="/facts/Electroluminescence/geazduXd">electroluminescence</a> and other electronic properties.<a class="footnote-ref" id="fnref:32" href="#fn:32"><sup>32</sup></a><a class="footnote-ref" id="fnref:33" href="#fn:33"><sup>33</sup></a> Siloles are efficient in electron transport. They owe their low lying <a href="/facts/LUMO/XyofpH0p">LUMO</a> to a favorable interaction between the <a href="/facts/Antibonding/9lhLNyt3">antibonding</a> <a href="/facts/Sigma_bond/CSyEe5CY">sigma</a> silicon orbital with an <a href="/facts/Antibonding/9lhLNyt3">antibonding</a> <a href="/facts/Pi_orbital/3Q6LAGYK">pi orbital</a> of the <a href="/facts/Butadiene/j9W2LxGv">butadiene</a> fragment. </p> <h3>Pentacoordinated silicon</h3> <p class="note">See also: <a href="/facts/Hypervalent_molecule/goPjlm9W">Hypervalent molecule § Pentacoordinated silicon</a></p> <p>Unlike carbon, silicon compounds can be coordinated to five atoms as well in a group of compounds ranging from so-called <a href="/facts/Silatrane/kAJvy5Ks">silatranes</a>, such as <a href="/facts/Phenylsilatrane/vp74C3AM">phenylsilatrane</a>, to a uniquely stable pentaorganosilicate:<a class="footnote-ref" id="fnref:34" href="#fn:34"><sup>34</sup></a> </p> <p>The stability of hypervalent silicon is the basis of the <a href="/facts/Hiyama_coupling/GmBLxC6n">Hiyama coupling</a>, a coupling reaction used in certain specialized organic synthetic applications. The reaction begins with the activation of a Si-C bond by <a href="/facts/Fluoride/LpqNMzwa">fluoride</a>: </p> R-SiR'3 + R"-X + F− → R-R" + R'3SiF + X− <h2 id="various-reactions">Various reactions</h2> <h3>Reactions of Si-C bonds</h3> <p>Unstrained silicon-carbon bonds are stable toward oxygen and water, at least under ambient conditions. Unsaturated silanes <a href="/facts/Electrophilic_substitution_of_unsaturated_silanes/lVyztUy1">are susceptible to electrophilic substitution</a>. Some strong acids will protodesilate arylsilanes and even some alkylsilanes. Most nucleophiles are too weak to displace carbon from silicon: the exceptions are <a href="/facts/Fluoride/LpqNMzwa">fluoride</a> ions and <a href="/facts/Alkoxide/RqG0rm1v">alkoxides</a>.<a class="footnote-ref" id="fnref:35" href="#fn:35"><sup>35</sup></a> </p> <h3>Reactions of Si-O and Si-halide bonds</h3> <p>Organosilicon halides and alkoxides will spontaneously hydrolyze.<a class="footnote-ref" id="fnref:36" href="#fn:36"><sup>36</sup></a> </p> <h3>Reactions of Si-Si bonds</h3> <p>Hexamethyldisilane reacts with <a href="/facts/Methyl_lithium/Fo5UzmsP">methyl lithium</a> to give trimethylsilyl lithium:<a class="footnote-ref" id="fnref:37" href="#fn:37"><sup>37</sup></a> </p> (CH3)6Si2 + CH3Li → (CH3)3SiLi + (CH3)4Si <p>Similarly, tris(trimethylsilyl)silyl lithium is derived from <a href="/facts/Tetrakis(trimethylsilyl)silane/AlCuqSNR">tetrakis(trimethylsilyl)silane</a>:<a class="footnote-ref" id="fnref:38" href="#fn:38"><sup>38</sup></a> </p> ((CH3)3Si)4Si + CH3Li → ((CH3)3Si)3SiLi + (CH3)4Si <h2 id="environmental-effects">Environmental effects</h2> <p>Organosilicon compounds affect bee (and other insect) immune expression, making them more susceptible to viral infection.<a class="footnote-ref" id="fnref:39" href="#fn:39"><sup>39</sup></a><a class="footnote-ref" id="fnref:40" href="#fn:40"><sup>40</sup></a> </p> <h2 id="see-also">See also</h2> <ul><li>Compounds of carbon with <a href="/facts/Period_3_element/1BE0Nc0K">period 3 elements</a>: <a href="/facts/Organoaluminum_compound/GM0K5eKE">organoaluminum compounds</a>, <a href="/facts/Organophosphorus_compound/kNgIF93U">organophosphorus compounds</a>, <a href="/facts/Organosulfur_compound/sUxSSXwD">organosulfur compounds</a></li> <li>Compounds of carbon with other <a href="/facts/Carbon_group/PkWCV3Vx">group 14</a> elements: <a href="/facts/Organogermanium_compound/KEBQDGLV">organogermanium compounds</a>, <a href="/facts/Organotin_compound/B4aDa9Lq">organotin compounds</a>, <a href="/facts/Organolead_compound/AB8GmFNF">organolead compounds</a></li> <li><a href="/facts/Silylene/HkSLM8q2">Silylenes</a>, the <a href="/facts/Carbene/3WxNSStY">carbene</a> counterparts</li> <li><a href="/facts/Silylenoid/p7harmJe">Silylenoids</a>, the <a href="/facts/Carbenoid/SMbPzaza">carbenoid</a> counterparts</li> <li><a href="/facts/Decamethylsilicocene/2fQ7oWdT">Decamethylsilicocene</a></li></ul> <h2 id="external-links">External links</h2> <ul><li>Magnus Walter's <a href="http://users.ox.ac.uk/~mwalter/web_05/resources/sil_chem/org_silicon_chem.shtml">Selected Aspects of Organosilicon Chemistry</a></li> <li><a href="http://www.chem.wisc.edu/areas/reich/OrgMet/silicon.htm">Silicon in organic synthesis</a></li> <li>S. Marsden (Editor): <a href="https://www.beilstein-journals.org/bjoc/series/1">Contemporary organosilicon chemistry.</a> Thematic Series in the Open Access Beilstein Journal of Organic Chemistry.</li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Muller, Richard (January 1965). "One hundred years of organosilicon chemistry". Journal of Chemical Education. 42 (1): 41. doi:10.1021/ed042p41. ISSN 0021-9584. <a href="https://pubs.acs.org/doi/abs/10.1021/ed042p41" target="_blank">https://pubs.acs.org/doi/abs/10.1021/ed042p41</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Muller, Richard (January 1965). "One hundred years of organosilicon chemistry". Journal of Chemical Education. 42 (1): 41. doi:10.1021/ed042p41. ISSN 0021-9584. <a href="https://pubs.acs.org/doi/abs/10.1021/ed042p41" target="_blank">https://pubs.acs.org/doi/abs/10.1021/ed042p41</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Thomas, Neil R. 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