Lithium tetramethylpiperidide

<h2 id="synthesis">Synthesis</h2>
<p>It is synthesised by the <a href="/facts/Deprotonation/SmUSh369">deprotonation</a> of <a href="/facts/2,2,6,6-tetramethylpiperidine/BHCQhrmV">2,2,6,6-tetramethylpiperidine</a> with <a href="/facts/N-Butyllithium/v4Rz4Dc1"><i>n</i>-butyllithium</a> at −78 °C. Recent reports show that this reaction can also be performed 0 °C.<a class="footnote-ref" id="fnref:1" href="#fn:1"><sup>1</sup></a> The compound is stable in a <a href="/facts/THF/P5t6SkMK">THF</a>/<a href="/facts/Ethylbenzene/aVhfY3vX">ethylbenzene</a> solvent mixture and is commercially available as such.
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<h2 id="structure">Structure</h2>
<p>Like many lithium reagents it has a tendency to aggregate, forming a <a href="/facts/Tetramer/qeUFnwC4">tetramer</a> in the solid state.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a>
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<h2 id="see-also">See also</h2>
<ul><li><a href="/facts/Lithium_diisopropylamide/5rcW8ERX">Lithium diisopropylamide</a></li>
<li><a href="/facts/Lithium_amide/o6oqNwWu">Lithium amide</a></li></ul>

<h2 id="references">References</h2>

<ol>
<li id="fn:1"><p>amide primer H. J. Reich 2002 <a href="http://www.chem.wisc.edu/areas/reich/Handouts/lireagents/amidebases.pdf" target="_blank">http://www.chem.wisc.edu/areas/reich/Handouts/lireagents/amidebases.pdf</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li>
<li id="fn:2"><p>M.F. Lappert; M.J. Slade; A. Singh; J.L. Atwood; R.D. Rogers; R. Shakir (1983). "Structure and reactivity of sterically hindered lithium amides and their diethyl etherates: crystal and molecular structures of [Li{N(SiMe3)2}(OEt2)]2 and tetrakis(2,2,6,6-tetramethylpiperidinatolithium)". Journal of the American Chemical Society. 105 (2): 302–304. doi:10.1021/ja00340a031. <a href="/wiki/Journal_of_the_American_Chemical_Society" target="_blank">/wiki/Journal_of_the_American_Chemical_Society</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li>
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Lithium tetramethylpiperidide open-in-new

Lithium tetramethylpiperidide