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iodine</div><style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"Iodane" redirects here. For the compound with that name, see <a href="/wiki/Hydrogen_iodide" title="Hydrogen iodide">Hydrogen iodide</a>.</div> <p>Unlike its lighter <a href="/wiki/Congener_(chemistry)" title="Congener (chemistry)">congeners</a>, the <a href="/wiki/Halogen" title="Halogen">halogen</a> <a href="/wiki/Iodine" title="Iodine">iodine</a> forms a number of stable <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a>, in which iodine exhibits higher <a href="/wiki/Formal_charge" title="Formal charge">formal</a> <a href="/wiki/Oxidation_state" title="Oxidation state">oxidation states</a> than -1 or <a href="/wiki/Coordination_number" title="Coordination number">coordination number</a> exceeding 1. These are the <b>hypervalent organoiodines</b>, often called <b>iodanes</b> after the <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> rule used to name them. </p><p>These iodine compounds are <a href="/wiki/Hypervalency" class="mw-redirect" title="Hypervalency">hypervalent</a> because the iodine atom formally contains in its <a href="/wiki/Valence_shell" class="mw-redirect" title="Valence shell">valence shell</a> more than the 8 electrons required for the <a href="/wiki/Octet_rule" title="Octet rule">octet rule</a>. Hypervalent iodine <a href="/wiki/Oxyanion" title="Oxyanion">oxyanions</a> are known for oxidation states +1, +3, +5, and +7; organic analogues of these moieties are known for each oxidation state except +7. </p><p>In terms of chemical behavior, λ<sup>3</sup>‑ and λ<sup>5</sup>‑iodanes are generally oxidizing and/or electrophilic species. They have been widely applied towards those ends in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hypervalent_organoiodine_compounds&action=edit&section=1" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several different naming conventions are in use for the hypervalent organoiodines. </p><p>All begin with nonstandard formal charge assignments. In iodane chemistry, carbon is considered <i>more</i> electronegative than iodine, despite the <a href="/wiki/Pauling_electronegativity" class="mw-redirect" title="Pauling electronegativity">Pauling electronegativities</a> of those respective atoms.<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> Thus <a href="/wiki/Iodobenzene" title="Iodobenzene">iodobenzene</a> (<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>I</span>) is an iodine(I) compound, <a href="/wiki/(Dichloroiodo)benzene" class="mw-redirect" title="(Dichloroiodo)benzene">(dichloroiodo)benzene</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>ICl<sub class="template-chem2-sub">2</sub></span>) and <a href="/wiki/Iodosobenzene" title="Iodosobenzene">iodosobenzene</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>IO</span>) iodine(III) compounds, and <a href="/wiki/Iodoxybenzene" class="mw-redirect" title="Iodoxybenzene">iodoxybenzene</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>IO<sub class="template-chem2-sub">2</sub></span>) an iodine(V) compound. </p><p>With that convention in place, IUPAC names assume complete electron transfer. Thus when iodine is ligated to an organic residue and two <a href="/wiki/Lewis_acids_and_bases" title="Lewis acids and bases">Lewis acids</a>, it is in the +3 <a href="/wiki/Oxidation_state" title="Oxidation state">oxidation state</a> and the corresponding compound is a <b>λ<sup>3</sup>‑iodane</b>. A compound with iodine(V) would be a <b>λ<sup>5</sup>‑iodane</b>, and a hypothetical iodine(VII)‑containing compound would be a <b>λ<sup>7</sup>‑iodane</b>. Organyl-iodine <a href="/wiki/Ether" title="Ether">ethers</a>, a kind of <b>λ<sup>3</sup>‑iodane</b>, are sometimes called <b>organic hypoiodites</b>. </p><p>Alternatively, the hypervalent iodines can be classified using <a href="/wiki/Electron_counting" title="Electron counting">neutral electron counting</a>. Iodine itself contains 7 valence electrons, and, in a monovalent iodane such as iodobenzene (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>I</span>), the <a href="/wiki/Phenyl_group" title="Phenyl group">phenyl</a> ligand donates one additional electron to give a completed octet. In a λ<sup>3</sup>‑iodane<b>,</b> each <a href="/w/index.php?title=X-type_ligand&action=edit&redlink=1" class="new" title="X-type ligand (page does not exist)">X-type ligand</a> donates an additional electron, for 10 in total; the result is a <b>decet</b> structure. Similarly, many λ<sup>5</sup>‑iodanes are <b>dodecet</b> molecules, and hypothetical λ<sup>7</sup>‑iodanes are <b>tetradecet</b> molecules. As with other hypervalent compounds, N‑X‑L notation can be used to describe the formal electron count of iodanes, in which N stands for the number of electrons around the central atom X (in this case iodine), and L is the total number of ligand bonds with X. Thus, λ<sup>3</sup>‑iodanes can be described as 10‑I‑3 compounds, λ<sup>5</sup>‑iodanes as 12‑I‑5 compounds, and hypothetical λ<sup>7</sup>‑iodanes as 14‑I‑7 compounds. </p> <div class="mw-heading mw-heading2"><h2 id="Electron_structure">Electron structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hypervalent_organoiodine_compounds&action=edit&section=2" title="Edit section: Electron structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As with other hypervalent compounds, iodanes bonding was formerly described using <a href="/wiki/D-orbital" class="mw-redirect" title="D-orbital"><i>d</i>-orbital</a> participation. <a href="/wiki/3-center-4-electron_bond" class="mw-redirect" title="3-center-4-electron bond">3-center-4-electron bonding</a> is now believed to be the primary bonding mode. This paradigm was developed by J.J. Musher in 1969. </p><p>One such bond exists in iodine(III) compounds, two such bonds reside in iodine(V) compounds and three such bonds would reside in the hypothetical iodine(VII) compounds. </p> <div class="mw-heading mw-heading2"><h2 id="Examples">Examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hypervalent_organoiodine_compounds&action=edit&section=3" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hypervalent organoiodine compounds are prepared by the oxidation of an <a href="/wiki/Organoiodine_chemistry" title="Organoiodine chemistry">organyl iodide</a>. </p><p> In 1886, German chemist <a href="/wiki/Conrad_Willgerodt" title="Conrad Willgerodt">Conrad Willgerodt</a> prepared the first hypervalent iodine compound, <a href="/wiki/Iodobenzene_dichloride" title="Iodobenzene dichloride">iodobenzene dichloride</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap"><a href="/wiki/Phenyl_group" title="Phenyl group">Ph</a><a href="/wiki/Iodine" title="Iodine">I</a><a href="/wiki/Chlorine" title="Chlorine">Cl</a><sub class="template-chem2-sub">2</sub></span>), by passing <a href="/wiki/Chlorine" title="Chlorine">chlorine</a> gas through <a href="/wiki/Iodobenzene" title="Iodobenzene">iodobenzene</a> in a cooled solution of <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>:<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></p><blockquote><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><p><span class="chemf nowrap"><a href="/wiki/Phenyl_group" title="Phenyl group">Ph</a><a href="/wiki/Iodine" title="Iodine">I</a> + <a href="/wiki/Chlorine" title="Chlorine">Cl</a><sub class="template-chem2-sub">2</sub> → PhICl<sub class="template-chem2-sub">2</sub></span></p></blockquote><p>This preparation can be varied to produce iodobenzene <a href="/wiki/Pseudohalide" class="mw-redirect" title="Pseudohalide">pseudohalides</a>. Cleaner preparations<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> begin with <a href="/wiki/Solution_(chemistry)" title="Solution (chemistry)">solutions</a> of <a href="/wiki/Peracetic_acid" title="Peracetic acid">peracetic acid</a> in <a href="/wiki/Glacial_acetic_acid" class="mw-redirect" title="Glacial acetic acid">glacial acetic acid</a>, also due to Willgerodt:<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><blockquote><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><p><span class="chemf nowrap"><a href="/wiki/Iodobenzene" title="Iodobenzene">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>I</a> + <a href="/wiki/Peracetic_acid" title="Peracetic acid">CH<sub class="template-chem2-sub">3</sub>C(O)OOH</a> + <a href="/wiki/Acetic_acid" title="Acetic acid">CH<sub class="template-chem2-sub">3</sub>COOH</a> → <a href="/wiki/(diacetoxyiodo)benzene" class="mw-redirect" title="(diacetoxyiodo)benzene">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>I(OC(O)CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></a> + <a href="/wiki/Water" title="Water">H<sub class="template-chem2-sub">2</sub>O</a></span></p></blockquote><p>The <a href="/wiki/Iodobenzene_diacetate" class="mw-redirect" title="Iodobenzene diacetate">iodobenzene diacetate</a> product hydrolyzes to the <a href="/wiki/Polymer" title="Polymer">polymeric</a> <a href="/wiki/Iodosobenzene" title="Iodosobenzene">iodosobenzene </a>(PhIO), which is stable in cool <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">alkaline solution</a>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> In hot water (or, in Willgerodt's original preparation, <a href="/wiki/Steam_distillation" title="Steam distillation">steam distillation</a>), iodosobenzene instead disproportionates to <a href="/wiki/Iodoxybenzene" class="mw-redirect" title="Iodoxybenzene">iodoxybenzene</a> and <a href="/wiki/Iodobenzene" title="Iodobenzene">iodobenzene</a>:<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">2 PhIO → PhIO<sub class="template-chem2-sub">2</sub> + PhI</span></dd></dl> <p>2-Iodobenzoic acid reacts with <a href="/wiki/Oxone" class="mw-redirect" title="Oxone">oxone</a><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> or a combination of potassium <a href="/wiki/Bromate" title="Bromate">bromate</a> and <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> to produce the <a href="/wiki/Solubility" title="Solubility">insoluble</a> λ<sup>5</sup>‑iodane <a href="/wiki/2-Iodoxybenzoic_acid" title="2-Iodoxybenzoic acid">2-iodoxybenzoic (IBX) acid</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> IBX acid is unstable and explosive, but <a href="/wiki/Acetylation" title="Acetylation">acetylation</a> tempers it to the stabler <a href="/wiki/Dess-Martin_periodinane" class="mw-redirect" title="Dess-Martin periodinane">Dess-Martin periodinane</a>.<sup id="cite_ref-Dess_Martin_1983_10-0" class="reference"><a href="#cite_note-Dess_Martin_1983-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Aliphatic_compound" title="Aliphatic compound">Aliphatic</a> <a href="/wiki/Hypoiodite" class="mw-redirect" title="Hypoiodite">hypoiodites</a> can be synthesized through a variant on the <a href="/wiki/Williamson_ether_synthesis" title="Williamson ether synthesis">Williamson ether synthesis</a>: an <a href="/wiki/Alkoxide" title="Alkoxide">alkoxide</a> reacts with <a href="/wiki/Iodine_monochloride" title="Iodine monochloride">iodine monochloride</a>, releasing the alkyl hypoiodite and <a href="/wiki/Chloride" title="Chloride">chloride</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Alternatively, the <a href="/wiki/Meyer-Hartmann_reaction" class="mw-redirect" title="Meyer-Hartmann reaction">Meyer-Hartmann reaction</a> applies: a silver alkoxide reacts with <a href="/wiki/Iodine" title="Iodine">elemental iodine</a> to give the hypoiodite and <a href="/wiki/Silver_iodide" title="Silver iodide">silver iodide</a>. They are <a href="/wiki/Photosensitive" class="mw-redirect" title="Photosensitive">unstable to visible light</a>, cleaving into <a href="/wiki/Alkoxyl" class="mw-redirect" title="Alkoxyl">alkoxyl</a> and <a href="/wiki/Iodine" title="Iodine">iodine</a> radicals.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>The synthesis of organyl periodyl derivatives (λ<sup>7</sup>-iodanes) has been attempted since the early 20th century.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Efforts so far have met with failure, although <a href="/wiki/Perchlorylbenzene" title="Perchlorylbenzene">aryl λ<sup>7</sup>‑chloranes</a> are known. Organic diesters of iodine(VII) are presumed intermediates in the periodate cleavage of diols (<a href="/wiki/Malaprade_reaction" title="Malaprade reaction">Malaprade reaction</a>), although no carbon-iodine(VII) bond is present in this process. </p> <div class="mw-heading mw-heading2"><h2 id="Diaryliodonium_salts">Diaryliodonium salts</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hypervalent_organoiodine_compounds&action=edit&section=4" title="Edit section: Diaryliodonium salts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><b>Diaryliodonium salts</b> are compounds of the type <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">[Ar−I<sup class="template-chem2-sup">+</sup>−Ar]X<sup class="template-chem2-sup">−</sup></span>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> They are formally composed of a diaryliodonium cation<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> paired with a <a href="/wiki/Counterion" title="Counterion">counteranion</a>, but crystal structures show a long, weak, partially-<a href="/wiki/Covalent" class="mw-redirect" title="Covalent">covalent</a> bond between the iodine and the counterion. Some authors have described this interaction as an example of <a href="/wiki/Halogen_bond" title="Halogen bond">halogen bonding</a>,<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> but the interaction exists even with traditionally <a href="/wiki/Non-coordinating_anion" title="Non-coordinating anion">noncoordinating ions</a>, such as <a href="/wiki/Perchlorate" title="Perchlorate">perchlorate</a>, <a href="/wiki/Triflate" title="Triflate">triflate</a>, or <a href="/wiki/Tetrafluoroborate" title="Tetrafluoroborate">tetrafluoroborate</a>.<sup id="cite_ref-:0_17-0" class="reference"><a href="#cite_note-:0-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> As a result, other authors regard the diaryliodonia as λ<sup>3</sup>-iodanes.<sup id="cite_ref-:1_18-0" class="reference"><a href="#cite_note-:1-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>The salts are generally T-shaped, with the counteranion occupying an apical position.<sup id="cite_ref-:1_18-1" class="reference"><a href="#cite_note-:1-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> The overall geometry at the iodine atom is <a href="/wiki/Trigonal_bipyramid_molecular_geometry" class="mw-redirect" title="Trigonal bipyramid molecular geometry">pseudotrigonal bipyramidal</a>. The placement of ligands exhibits <a href="/wiki/Apicophilicity" title="Apicophilicity">apicophilicity</a>: the <a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a> group and chlorine group attain apical positions, while the other phenyl group and a <a href="/wiki/Lone_pair" title="Lone pair">lone pair</a> of electrons hold equatorial ones. </p><p>Salts with a halide counterion are poorly soluble in many organic solvents, possibly because the halides bridge <a href="/wiki/Dimerization_(chemistry)" class="mw-redirect" title="Dimerization (chemistry)">dimers</a>. Solubility improves with <a href="/wiki/Triflate" title="Triflate">triflate</a> and <a href="/wiki/Tetrafluoroborate" title="Tetrafluoroborate">tetrafluoroborate</a> counterions.<sup id="cite_ref-:0_17-1" class="reference"><a href="#cite_note-:0-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>In general, the salts can be prepared from preformed hypervalent iodines such as <a href="/wiki/Iodic_acid" title="Iodic acid">iodic acid</a>, <a href="/w/index.php?title=Iodosyl_sulfate&action=edit&redlink=1" class="new" title="Iodosyl sulfate (page does not exist)">iodosyl sulfate</a> or <a href="/w/index.php?title=Iodosyl_triflate&action=edit&redlink=1" class="new" title="Iodosyl triflate (page does not exist)">iodosyl triflate</a>. The first such compound was synthesised in 1894, via the <a href="/wiki/Silver_hydroxide" class="mw-redirect" title="Silver hydroxide">silver hydroxide</a>-catalyzed coupling of two aryl iodides (the <b>Meyer–Hartmann reaction</b>):<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Meyer-Hartmann-Reaktion_Uebersichtsreaktion_V1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Meyer-Hartmann-Reaktion_Uebersichtsreaktion_V1.svg/400px-Meyer-Hartmann-Reaktion_Uebersichtsreaktion_V1.svg.png" decoding="async" width="400" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Meyer-Hartmann-Reaktion_Uebersichtsreaktion_V1.svg/600px-Meyer-Hartmann-Reaktion_Uebersichtsreaktion_V1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Meyer-Hartmann-Reaktion_Uebersichtsreaktion_V1.svg/800px-Meyer-Hartmann-Reaktion_Uebersichtsreaktion_V1.svg.png 2x" data-file-width="1098" data-file-height="234" /></a><figcaption></figcaption></figure> <p>Alternatively, the iodane may be formed <i>in situ</i>: an aryl iodide is oxidized to an aryliodine(III) compound (such as ArIO), followed by a <a href="/wiki/Ligand_exchange" class="mw-redirect" title="Ligand exchange">ligand exchange</a>. The latter can occur with organometallized arenes such as an <a href="/wiki/Arylstannane" class="mw-redirect" title="Arylstannane">arylstannane</a> or <a href="/wiki/Arylsilane" class="mw-redirect" title="Arylsilane">-silane</a> (a <a href="/wiki/Nucleophilic_aromatic_substitution" title="Nucleophilic aromatic substitution">nucleophilic aromatic substitution</a> reaction) or unfunctionalized arenes in the presence of a Brønsted or Lewis acid (an <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">electrophilic aromatic substitution</a> reaction). </p><p>Diaryliodonium salts react with <a href="/wiki/Nucleophile" title="Nucleophile">nucleophiles</a> at iodine, replacing one ligand to form the substituted arene ArNu and iodobenzene ArI. Diaryliodonium salts also react with metals M through ArMX intermediates in <a href="/wiki/Cross-coupling_reaction" title="Cross-coupling reaction">cross-coupling reactions</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hypervalent_organoiodine_compounds&action=edit&section=5" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:HypervalentIodineCNbondFormation.png" class="mw-file-description"><img alt="Hypervalent iodine(III)-catalyzed C–N bond forming reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/HypervalentIodineCNbondFormation.png/400px-HypervalentIodineCNbondFormation.png" decoding="async" width="400" height="303" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/HypervalentIodineCNbondFormation.png/600px-HypervalentIodineCNbondFormation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/63/HypervalentIodineCNbondFormation.png/800px-HypervalentIodineCNbondFormation.png 2x" data-file-width="1013" data-file-height="768" /></a><figcaption><a href="/wiki/Sacrificial_catalyst" class="mw-redirect" title="Sacrificial catalyst">Sacrificial catalyst</a> <a href="/wiki/MCPBA" class="mw-redirect" title="MCPBA">mCPBA</a> oxidizes an aryliodide reagent to iodine(III) intermediate <b>A</b>. <b>A</b> in turn converts the hydroxylamine group to a <a href="/wiki/Nitrenium_ion" title="Nitrenium ion">nitrenium ion</a>, <b>B</b>. The nitrenium is performs <a href="/wiki/Electrophile" title="Electrophile">electrophilic</a> <a href="/wiki/Arene_substitution_patterns" class="mw-redirect" title="Arene substitution patterns">ipso</a> addition to the aromatic ring, forming an <a href="/wiki/Enone" class="mw-redirect" title="Enone">enonic</a> <a href="/wiki/Lactam" title="Lactam">lactam</a>.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Hypervalent iodine compounds are predominantly used as <a href="/wiki/Oxidizing_agent" title="Oxidizing agent">oxidizing reagents</a>, although they are specialized and expensive. In some cases they replace more toxic oxidants.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Iodobenzene_diacetate" class="mw-redirect" title="Iodobenzene diacetate">Iodobenzene diacetate</a> (PhIAc<sub>2</sub>) and <a href="/wiki/(Bis(trifluoroacetoxy)iodo)benzene" title="(Bis(trifluoroacetoxy)iodo)benzene">iodobenzene di(trifluoroacetate)</a> are both strong oxidizing agents used in <a href="/wiki/Organic_oxidation" class="mw-redirect" title="Organic oxidation">organic oxidations</a>, as well as precursors for further organoiodine compounds. A <a href="/wiki/Hypervalent_iodine" class="mw-redirect" title="Hypervalent iodine">hypervalent iodine</a> (III) reagent was used as oxidant, together with ammonium acetate as nitrogen source, to provide <a href="/wiki/2-Furonitrile" title="2-Furonitrile">2-Furonitrile</a>, a pharmaceutical intermediate and potential artificial sweetener.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Current research focuses on the use of iodanes in <a href="/wiki/Carbon-carbon_bond" class="mw-redirect" title="Carbon-carbon bond">carbon-carbon</a> and carbon-heteroatom <a href="/wiki/Coupling_reaction" title="Coupling reaction">bond-forming reactions</a>. In one study, an <a href="/wiki/Intramolecular_reaction" title="Intramolecular reaction">intramolecular</a> C-N coupling of an <a href="/wiki/Alkoxyhydroxylamine" class="mw-redirect" title="Alkoxyhydroxylamine">alkoxyhydroxylamine</a> to its <a href="/wiki/Anisole" title="Anisole">anisole</a> group is accomplished with a catalytic amount of aryliodide in <a href="/wiki/Trifluoroethanol" class="mw-redirect" title="Trifluoroethanol">trifluoroethanol</a>.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hypervalent_organoiodine_compounds&action=edit&section=6" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Carbonyl_oxidation_with_hypervalent_iodine_reagents" title="Carbonyl oxidation with hypervalent iodine reagents">Carbonyl oxidation with hypervalent iodine reagents</a></li> <li><a href="/wiki/Phenol_oxidation_with_hypervalent_iodine_reagents" title="Phenol oxidation with hypervalent iodine reagents">Phenol oxidation with hypervalent iodine reagents</a></li></ul> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hypervalent_organoiodine_compounds&action=edit&section=7" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist 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data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREF(Anastasios)1997" class="citation book cs1">(Anastasios), Varvoglis, A. 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"Diaryliodonium Salts: A Journey from Obscurity to Fame". <i><a href="/wiki/Angew._Chem._Int._Ed." class="mw-redirect" title="Angew. Chem. Int. Ed.">Angew. Chem. Int. Ed.</a></i> <b>48</b> (48): <span class="nowrap">9052–</span>9070. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.200904689">10.1002/anie.200904689</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19876992">19876992</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angew.+Chem.+Int.+Ed.&rft.atitle=Diaryliodonium+Salts%3A+A+Journey+from+Obscurity+to+Fame&rft.volume=48&rft.issue=48&rft.pages=%3Cspan+class%3D%22nowrap%22%3E9052-%3C%2Fspan%3E9070&rft.date=2009&rft_id=info%3Adoi%2F10.1002%2Fanie.200904689&rft_id=info%3Apmid%2F19876992&rft.aulast=Merritt&rft.aufirst=Eleanor+A.&rft.au=Olofsson%2C+Berit&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHypervalent+organoiodine+compounds" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text">Note that in the diaryliodonium salt description, the compound is <i>not</i> hypervalent, and the bonding number is the standard one for iodine (λ<sup>1</sup>). It is a 8-I-2 species. In the other common description of these compounds as covalent iodanes, they are formally 10-I-3 and λ<sup>3</sup>.</span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFResnatiUrsiniPilatiPolitzer2017" class="citation journal cs1">Resnati, G.; Ursini, M.; Pilati, T.; Politzer, P.; Murray, J. S.; Cavallo, G. 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"First hypervalent iodine(III)-catalyzed C-N bond forming reaction: catalytic spirocyclization of amides to N-fused spirolactams". <i><a href="/wiki/Chemical_Communications" class="mw-redirect" title="Chemical Communications">Chemical Communications</a></i>. <b>44</b> (12): <span class="nowrap">1224–</span>1226. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fb616510a">10.1039/b616510a</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17356763">17356763</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Communications&rft.atitle=First+hypervalent+iodine%28III%29-catalyzed+C-N+bond+forming+reaction%3A+catalytic+spirocyclization+of+amides+to+N-fused+spirolactams&rft.volume=44&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1224-%3C%2Fspan%3E1226&rft.date=2007&rft_id=info%3Adoi%2F10.1039%2Fb616510a&rft_id=info%3Apmid%2F17356763&rft.aulast=Dohi&rft.aufirst=T.&rft.au=Maruyama%2C+A.&rft.au=Minamitsuji%2C+Y.&rft.au=Takenaga%2C+N.&rft.au=Kita%2C+Y.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHypervalent+organoiodine+compounds" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hypervalent_organoiodine_compounds&action=edit&section=8" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://www.organic-chemistry.org/Highlights/2005/25May.shtm">Hypervalent Iodine Chemistry</a></li></ul>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Hypervalent_organoiodine_compounds&oldid=1266685504">https://en.wikipedia.org/w/index.php?title=Hypervalent_organoiodine_compounds&oldid=1266685504</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Iodanes" title="Category:Iodanes">Iodanes</a></li><li><a href="/wiki/Category:Oxidizing_agents" title="Category:Oxidizing agents">Oxidizing agents</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">CS1 maint: multiple names: authors list</a></li><li><a href="/wiki/Category:CS1_German-language_sources_(de)" title="Category:CS1 German-language sources (de)">CS1 German-language sources (de)</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 1 January 2025, at 19:55<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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