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Hexamethyldisilane
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<h2 id="synthesis-and-reactions">Synthesis and reactions</h2> <p>Hexamethyldisilane can be produced by <a href="/facts/Wurtz_reaction/teXQemUj">Wurtz-like coupling</a> of trimethylsilyl chloride in the presence of a reducing agent such as <a href="/facts/Potassium_graphite/FssMzW21">potassium graphite</a>: </p> 2 Me3SiCl + 2 K → Me3Si−SiMe3 + 2 KCl <p>With an excess of the reductant, the alkali metal silyl derivative is produced:<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a> </p> Me3Si−SiMe3 + 2 K → 2 Me3SiK <p>The Si-Si bond in hexamethyldisilane is cleaved by strong nucleophiles and electrophiles. Alkyl lithium compounds react as follows: </p> Si2Me6 + RLi → RSiMe3 + LiSiMe3 <p><a href="/facts/Iodine/JlfMecMf">Iodine</a> gives <a href="/facts/Trimethylsilyl_iodide/muHEvTal">trimethylsilyl iodide</a>.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> </p> Me3Si−SiMe3 + I2 → 2 SiMe3I <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Tamejiro Hiyama, Manabu Kuroboshi, "Hexamethyldisilane" Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons. doi:10.1002/047084289X.rh015 <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Fürstner, Alois; Weidmann, Hans (1988). "Efficient formation and cleavage of disilanes by potassium-graphite. Silylation with silyl metal reagents". Journal of Organometallic Chemistry. 354: 15–21. doi:10.1016/0022-328X(88)80634-X. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Olah, G.; Narang, S.C. (1982). "Iodotrimethylsilane—a versatile synthetic reagent". Tetrahedron. 38 (15): 2225. doi:10.1016/0040-4020(82)87002-6. <a href="/wiki/Tetrahedron_(journal)" target="_blank">/wiki/Tetrahedron_(journal)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> </ol>