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Organogallium chemistry
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<h2 id="organogalliumi-chemistry">Organogallium(I) chemistry</h2> <p><a href="/facts/Organometallic_complex/bhqFz2P0">Organometallic complexes</a> of gallium(I) are significantly rarer than that of gallium(III). Some common species include <a href="/facts/Aromatic_compound/3EXq8Tgf">arene</a>-gallium(I) complexes and <a href="/facts/Sterically_hindered/TnX5c8HG">sterically hindered</a> <a href="/facts/Aryl_group/M3z7QRXd">aryl</a> gallium(I) complexes.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a><a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a></p> <h2 id="organogalliumiii-chemistry">Organogallium(III) chemistry</h2> <p>Compounds of the type R3Ga are monomeric. <a href="/facts/Lewis_acid/qlLqRvg2">Lewis acidity</a> decreases in the order Al > Ga > In and as a result organogallium compounds do not form bridged dimers as organoaluminum compounds do. Organogallium compounds are also less reactive than <a href="/facts/Organoaluminum_compounds/GM0K5eKE">organoaluminum compounds</a>. They do form stable peroxides.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p><p>Organogallium compounds can be synthesized by <a href="/facts/Transmetallation/Mm0hQzp3">transmetallation</a>, for example the reaction of gallium metal with <a href="/facts/Dimethylmercury/ettgPTS7">dimethylmercury</a>: </p> 2Ga + 3Me2Hg → 2Me3Ga + 3 Hg <p>or via <a href="/facts/Organolithium/xgYnjhP3">organolithium</a> compounds or <a href="/facts/Grignard_reaction/DfhXQ6SG">Grignards</a>: </p> GaCl3 + 3MeMgBr → Me3Ga + 3MgBrCl <p>The electron-deficient nature of gallium can be removed by <a href="/facts/Complex_formation/1tCyeQUm">complex formation</a>, for example </p> Me2GaCl + NH3 → [Me2Ga(NH3)Cl]+Cl− <p><a href="/facts/Dewar%E2%80%93Chatt%E2%80%93Duncanson_model/h7VTIqyV">Pi complex</a> formation with <a href="/facts/Alkyne/VHI4N5Wo">alkynes</a> is also known. </p><p>Organogallium compounds are reagents or intermediates in several classes of organic reactions: </p> <ul><li><a href="/facts/Barbier_reaction/QjDsgIsl">Barbier-type</a> reactions with elemental gallium, allylic substrates and carbonyl compounds</li> <li><a href="/facts/Carbometallation/PPA3WdMv">Carbometallation</a> (carbogallation) reactions <a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a></li></ul> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Organoindium_chemistry/bGh2jTpj">Organoindium chemistry</a></li> <li><a href="/facts/Organothallium_chemistry/IMf5V6y1">Organothallium chemistry</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>C. Elschenbroich, A. Salzer Organometallics : A Concise Introduction (2nd Ed) (1992) from Wiley-VCH: Weinheim. ISBN 3-527-28165-7 <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Chemistry of aluminium, gallium, indium, and thallium Anthony John Downs (Ed.) ISBN 978-0-7514-0103-5, 1993 <a href="/wiki/ISBN_(identifier)" target="_blank">/wiki/ISBN_(identifier)</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Greenwood (2001). Chemistry of the Elements (2nd ed.). Elsevier. pp. 262–265. ISBN 0-7506-3365-4. <a href="0-7506-3365-4" target="_blank">0-7506-3365-4</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Housecroft, Catherine E. (2018). Inorganic chemistry (Fifth ed.). Harlow, England ; New York: Pearson. pp. 887–892. ISBN 978-1-292-13414-7. <a href="978-1-292-13414-7" target="_blank">978-1-292-13414-7</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>W, Uhl and M. R. Halvagar; et al. (2009). "Reducing Ga-H and Ga-C Bonds in Close Proximity to Oxidizing Peroxo Groups: Conflicting Properties in Single Molecules". Chemistry: A European Journal. 15 (42): 11298–11306. doi:10.1002/chem.200900746. PMID 19780106. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Amemiya Ryo, Yamaguchi Masahiko (2005). "GaCl3 in Organic Synthesis". Eur. J. Org. Chem. 2005 (24): 5145–5150. doi:10.1002/ejoc.200500512. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> </ol>