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<span id="openzim-page-title" class="mw-page-title-main"><span class="mw-page-title-main">Phosphinite</span></span>
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</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="Phosphonite" title="Phosphonite">phosphonite</a> (formula P(OR)<sub>2</sub>R) .</div>
<p>In <a href="Organic_chemistry" title="Organic chemistry">organic chemistry</a>, <b>phosphinites</b> are <a href="Organophosphorus" class="mw-redirect" title="Organophosphorus">organophosphorus</a> compounds with the formula <style data-mw-deduplicate="TemplateStyles:r1123817410">
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</style><span class="chemf nowrap">P(OR)R<sub class="template-chem2-sub">2</sub></span>. They are used as ligands in <a href="Homogeneous_catalysis" title="Homogeneous catalysis">homogeneous catalysis</a> and <a href="Coordination_chemistry" class="mw-redirect" title="Coordination chemistry">coordination chemistry</a>.<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>
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<div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2></div>
<p>Phosphinites are prepared by <a href="Alcoholysis" class="mw-redirect" title="Alcoholysis">alcoholysis</a> of organophosphinous chlorides. For example, treatment of <a href="Chlorodiphenylphosphine" title="Chlorodiphenylphosphine">chlorodiphenylphosphine</a> with <a href="Methanol" title="Methanol">methanol</a> and base gives methyl diphenylphosphinite:
</p>
<dl><dd>ClPPh<sub>2</sub> + CH<sub>3</sub>OH → CH<sub>3</sub>OPPh<sub>2</sub> + HCl</dd></dl>
<p>Although they are <a href="Ester" title="Ester">esters</a> of <a href="Phosphinous_acids" title="Phosphinous acids">phosphinous acids</a> (R<sub>2</sub>POH), phosphinites are not made via such intermediates.
</p>
<div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2></div>
<p>Oxidation of phosphinites gives <a href="Phosphinate" title="Phosphinate">phosphinates</a>:
</p>
<dl><dd>2 P(OR)R<sub>2</sub> + O<sub>2</sub> → 2 OP(OR)R<sub>2</sub></dd></dl>
<p>Phosphinites are ligands, giving derivatives similar to <a href="Metal_phosphine_complex" class="mw-redirect" title="Metal phosphine complex">metal phosphine complexes</a>. They are stronger pi-acceptors than typical phosphine ligands.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
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<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>
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<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">
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</style><cite id="CITEREFD._E._C._Corbridge1995" class="citation book cs1">D. E. C. Corbridge (1995). <i>Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology</i> (5th ed.). Amsterdam: Elsevier. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>0-444-89307-5</bdi>.</cite></span>
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<li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><cite id="CITEREFRajanbabu2012" class="citation book cs1">Rajanbabu, T. V. Babu (2012). "Phosphinite and Phosphonite Ligands". <i>Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis</i>. pp. <span class="nowrap">159–</span>232. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9781118299715.ch5">10.1002/9781118299715.ch5</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>9781118299715</bdi>.</cite></span>
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<div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2></div>
<ul><li><a href="Phosphine" title="Phosphine">Phosphine</a> - PR<sub>3</sub></li>
<li><a href="Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a> - OPR<sub>3</sub></li>
<li><a href="Phosphonite" title="Phosphonite">Phosphonite</a> - P(OR)<sub>2</sub>R</li>
<li><a href="Phosphite" class="mw-redirect" title="Phosphite">Phosphite</a> - P(OR)<sub>3</sub></li>
<li><a href="Phosphinate" title="Phosphinate">Phosphinate</a> - OP(OR)R<sub>2</sub></li>
<li><a href="Phosphonate" title="Phosphonate">Phosphonate</a> - OP(OR)<sub>2</sub>R</li>
<li><a href="Phosphate" title="Phosphate">Phosphate</a> - OP(OR)<sub>3</sub></li></ul>
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</style><div id="Organophosphorus47" style="font-size:114%;margin:0 4em"><a href="Organophosphorus_chemistry" title="Organophosphorus chemistry">Organophosphorus</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="Phosphite_anion" class="mw-redirect" title="Phosphite anion">PO<sub>3</sub>H<sup>2−</sup></a></li>
<li><a href="Phosphite_ester" title="Phosphite ester">P(O–)<sub>3</sub></a></li>
<li><a href="Phosphoric_acids_and_phosphates" title="Phosphoric acids and phosphates">P<sub>2</sub>O<sub>5</sub>·<span class="texhtml mvar" style="font-style:italic;">n</span>H<sub>2</sub>O</a></li>
<li><a href="Organophosphate" title="Organophosphate">OP(O–)<sub>3</sub></a></li>
<li>–P(OH)<sub>2</sub></li>
<li><a href="Phosphonite" title="Phosphonite">–P(O–)<sub>2</sub></a></li>
<li><a href="Phosphonate" title="Phosphonate">–P(O)(O–)<sub>2</sub></a></li>
<li>
<ul><li>free acid <a href="Phosphinous_acids" title="Phosphinous acids">HOP(CF<sub>3</sub>)<sub>2</sub></a></li></ul></li>
<li><a href="Organophosphinic_acid" title="Organophosphinic acid">HOP(O)<</a></li>
<li><a href="Phosphinate" title="Phosphinate">PO<sub>2</sub>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></a></li>
<li><a href="Organophosphine" title="Organophosphine">–P<</a></li>
<li><a href="Phosphine_oxides" title="Phosphine oxides">–P(O)<</a></li>
<li><a href="Phosphoramidite" title="Phosphoramidite">(–O)<sub>2</sub>PN<</a>
<ul><li>e.g. <a href="Nucleoside_phosphoramidite" title="Nucleoside phosphoramidite">Nucleoside phosphoramidite</a></li></ul></li>
<li><a href="Phosphoramidate" title="Phosphoramidate">(–O)<sub>2</sub>P(O)N<</a>
<ul><li>e.g. <a href="Phosphocreatine" title="Phosphocreatine">Phosphocreatine</a></li></ul></li>
<li>–OP(N<)<sub>2</sub></li>
<li><a href="Phosphoramidate" title="Phosphoramidate">–OP(O)(N<)<sub>2</sub></a>
<ul><li>e.g. <a href="Morpholino" title="Morpholino">Morpholino</a></li>
<li><a href="Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li></ul></li>
<li><a href="Aminophosphine" title="Aminophosphine">P(N<)<sub>3</sub></a>
<ul><li>e.g. <a href="Tris(dimethylamino)phosphine" title="Tris(dimethylamino)phosphine">P(NMe<sub>2</sub>)<sub>3</sub></a></li></ul></li>
<li><a href="Phosphoramides" title="Phosphoramides">OP(N<)<sub>3</sub></a>
<ul><li>e.g. <a href="Hexamethylphosphoramide" title="Hexamethylphosphoramide">Hexamethylphosphoramide</a></li>
<li><a href="Metepa" title="Metepa">Metepa</a></li></ul></li>
<li>–NP(N<)<sub>3</sub></li>
<li><a href="Phosphonamidate" class="mw-redirect" title="Phosphonamidate">–P(O)(O–)N<</a></li>
<li>–P(O)(N<)<sub>2</sub></li>
<li>>P(O)N<</li>
<li><a href="Thiophosphate" title="Thiophosphate">PS<sub><span class="texhtml mvar" style="font-style:italic;">x</span></sub>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">3−</sup><br><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"><span class="texhtml">4-<i>x</i></span></sub></span></span></a></li>
<li><a href="Organothiophosphate" title="Organothiophosphate">(–O)<sub>3</sub>PS</a></li>
<li><a href="Cyclophosphines" class="mw-redirect" title="Cyclophosphines">(-P)<sub>5</sub></a></li></ul>
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