Abstract
<jats:title>Abstract</jats:title> <jats:p> <jats:chem-struct-wrap> <jats:chem-struct> <jats:graphic xmlns:xlink="http://www.w3.org/1999/xlink" position="anchor" xlink:href="urn:x-wiley:9780470842898:media:rd005m:nrd005msf.001"> <jats:alt-text>image</jats:alt-text> </jats:graphic> </jats:chem-struct> </jats:chem-struct-wrap> <jats:table-wrap position="anchor"> <jats:table frame="hsides"> <jats:col/> <jats:col/> <jats:col/> <jats:tbody> <jats:tr> <jats:td> <jats:italic>[</jats:italic> <jats:ext-link xmlns:xlink="http://www.w3.org/1999/xlink" ext-link-type="cas-registration-number" xlink:href="3240-34-4"> <jats:italic>3240‐34‐4</jats:italic> </jats:ext-link> <jats:italic>]</jats:italic> </jats:td> <jats:td> C <jats:sub>10</jats:sub> H <jats:sub>11</jats:sub> IO <jats:sub>4</jats:sub> </jats:td> <jats:td>(MW 322.10)</jats:td> </jats:tr> </jats:tbody> </jats:table> </jats:table-wrap> </jats:p> <jats:p> InChI = <jats:ext-link xmlns:xlink="http://www.w3.org/1999/xlink" ext-link-type="inchi" xlink:href="InChI=1S/C10H11IO4/c1-8(12)14-11(15-9(2)13)10-6-4-3-5-7-10/h3-7H,1-2H3">1S/C10H11IO4/c1‐8(12)14‐11(15‐9(2)13)10‐6‐4‐3‐5‐7‐10/h3‐7H,1‐2H3</jats:ext-link> </jats:p> <jats:p> InChIKey = <jats:ext-link xmlns:xlink="http://www.w3.org/1999/xlink" ext-link-type="inchi" xlink:href="InChIKey=ZBIKORITPGTTGI-UHFFFAOYSA-N">ZBIKORITPGTTGI‐UHFFFAOYSA‐N</jats:ext-link> </jats:p> <jats:p> (transannular carbocyclization, <jats:sup> <jats:bold>6</jats:bold> </jats:sup> <jats:italic>vic</jats:italic> ‐diazide formation, <jats:sup> <jats:bold>7</jats:bold> </jats:sup> α‐hydroxy dimethyl acetal formation, <jats:sup> <jats:bold>8,10,11,13</jats:bold> </jats:sup> oxetane formation, <jats:sup> <jats:bold>9</jats:bold> </jats:sup> chromone, flavone, chalcone oxidation, <jats:sup> <jats:bold>11,12</jats:bold> </jats:sup> arene–Cr(CO) <jats:sub>3</jats:sub> functionalization, <jats:sup> <jats:bold>14</jats:bold> </jats:sup> phenolic oxidation <jats:sup> <jats:bold>16</jats:bold> </jats:sup> and coupling, <jats:sup> <jats:bold>17,18</jats:bold> </jats:sup> lactol fragmentation, <jats:sup> <jats:bold>19</jats:bold> </jats:sup> iodonium ylides and intramolecular cyclopropanation, <jats:sup> <jats:bold>20</jats:bold> </jats:sup> oxidation of amines <jats:sup> <jats:bold>24–28</jats:bold> </jats:sup> and indoles, <jats:sup> <jats:bold>30,31</jats:bold> </jats:sup> hydrazine derivatives (diimide <jats:sup> <jats:bold>32</jats:bold> </jats:sup> and azodicarbonyls <jats:sup> <jats:bold>33</jats:bold> </jats:sup> ) and radical type intramolecular oxide formation <jats:sup> <jats:bold>44–46</jats:bold> </jats:sup> ). </jats:p> <jats:p> <jats:list list-type="simple"> <jats:list-item> <jats:p> <jats:italic>Alternate Names:</jats:italic> phenyliodine(III) diacetate; DIB; iodobenzene diacetate; IBD. </jats:p> </jats:list-item> <jats:list-item> <jats:p> <jats:italic>Physical Data:</jats:italic> mp 163–165 °C. </jats:p> </jats:list-item> <jats:list-item> <jats:p> <jats:italic>Solubility:</jats:italic> sol AcOH, MeCN, CH <jats:sub>2</jats:sub> Cl <jats:sub>2</jats:sub> ; in KOH or NaHCO <jats:sub>3</jats:sub> /MeOH it is equivalent to PhI(OH) <jats:sub>2</jats:sub> . </jats:p> </jats:list-item> <jats:list-item> <jats:p> <jats:italic>Form Supplied in:</jats:italic> commercially available as a white solid. </jats:p> </jats:list-item> <jats:list-item> <jats:p> <jats:italic>Preparative Method:</jats:italic> by reaction of iodobenzene with <jats:bold> <jats:italic>Peracetic Acid</jats:italic> </jats:bold> . <jats:sup> <jats:bold>4,5</jats:bold> </jats:sup> </jats:p> </jats:list-item> <jats:list-item> <jats:p> <jats:italic>Purification:</jats:italic> recrystallization from 5 M acetic acid. <jats:sup> <jats:bold>4</jats:bold> </jats:sup> </jats:p> </jats:list-item> <jats:list-item> <jats:p> <jats:italic>Handling, Storage, and Precautions:</jats:italic> a stable compound which can be stored indefinitely. </jats:p> </jats:list-item> </jats:list> </jats:p>