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searchaux" style="display:none">Functional group</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Thiosulfinate-ester-general-2D.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Thiosulfinate-ester-general-2D.png/150px-Thiosulfinate-ester-general-2D.png" decoding="async" width="150" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Thiosulfinate-ester-general-2D.png/225px-Thiosulfinate-ester-general-2D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Thiosulfinate-ester-general-2D.png/300px-Thiosulfinate-ester-general-2D.png 2x" data-file-width="1356" data-file-height="885" /></a><figcaption>General structure of a thiosulfinate, drawn in <a href="/wiki/Expanded_octet" class="mw-redirect" title="Expanded octet">expanded octet</a> style<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></figcaption></figure> <p>In <a href="/wiki/Organosulfur_chemistry" title="Organosulfur chemistry">organosulfur chemistry</a>, <b>thiosulfinate</b> is a <a href="/wiki/Functional_group" title="Functional group">functional group</a> consisting of the linkage R-S(O)-S-R (R refers to organic substituents). Thiolsulfinates are also named as alkanethiosulfinic (or arenethiosulfinic) acid esters. </p><p>They are the first of the series of functional groups containing an oxidized <a href="/wiki/Disulfide" title="Disulfide">disulfide</a> bond. Other members of this family include <a href="/wiki/Thiosulfonate" title="Thiosulfonate">thiosulfonates</a> (R-SO<sub>2</sub>-S-R), α-disulfoxides (R-S(O)-S(O)-R), <a href="/wiki/Sulfinyl_sulfone" class="mw-redirect" title="Sulfinyl sulfone">sulfinyl sulfones</a> (R-S(O)-SO<sub>2</sub>-R), and α-disulfones (R-SO<sub>2</sub>-SO<sub>2</sub>-R), of which all (except α‑disulfoxides<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>) are known. The thiosulfinate group can occur in cyclic as well as acyclic structures.<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><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><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> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Occurrence">Occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thiosulfinate&action=edit&section=1" title="Edit section: Occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:R-allicin-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/R-allicin-2D-skeletal.svg/220px-R-allicin-2D-skeletal.svg.png" decoding="async" width="220" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/R-allicin-2D-skeletal.svg/330px-R-allicin-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b5/R-allicin-2D-skeletal.svg/440px-R-allicin-2D-skeletal.svg.png 2x" data-file-width="1100" data-file-height="423" /></a><figcaption>Allicin</figcaption></figure> <p>A variety of acyclic and cyclic thiosulfinates are found in plants, or formed when the plants are cut or crushed. </p><p>A well-known thiosulfinate is <a href="/wiki/Allicin" title="Allicin">allicin</a>, one of the active ingredients formed when <a href="/wiki/Garlic" title="Garlic">garlic</a> is crushed. Allicin was discovered in 1944 by <a href="/wiki/Chester_J._Cavallito" class="mw-redirect" title="Chester J. Cavallito">Chester J. Cavallito</a> and coworkers. Thiosulfinates containing various combinations of the <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a>, <a href="/wiki/N-propyl" class="mw-redirect" title="N-propyl"><i>n</i>-propyl</a>, <a href="/wiki/1-propenyl" class="mw-redirect" title="1-propenyl">1-propenyl</a>, <a href="/wiki/2-propenyl" class="mw-redirect" title="2-propenyl">2-propenyl</a>, <a href="/wiki/N-butyl" class="mw-redirect" title="N-butyl"><i>n</i>-butyl</a>, 1-butenyl and <a href="/wiki/2-butenyl" class="mw-redirect" title="2-butenyl">2-butenyl</a> groups are formed upon crushing different <i><a href="/wiki/Allium" title="Allium">Allium</a></i> as well as <i><a href="/wiki/Brassica" title="Brassica">Brassica</a></i> species.<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><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><p>Zeylanoxides are cyclic thiosulfinates containing the 1,2-<a href="/wiki/Dithiolane" title="Dithiolane">dithiolane</a>-1-oxide ring, isolated from the tropical weed <i><a href="/wiki/Sphenoclea_zeylanica" title="Sphenoclea zeylanica">Sphenoclea zeylanica</a></i>. These heterocyclic thiosulfinates are <a href="/wiki/Chiral" class="mw-redirect" title="Chiral">chiral</a> at carbon as well as at sulfur.<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> </p><p>Crushing the roots of <i><a href="/wiki/Petiveria_alliacea" class="mw-redirect" title="Petiveria alliacea">Petiveria alliacea</a></i> affords the thiosulfinates <i>S</i>-(2-hydroxyethyl) 2-hydroxyethane)thiosulfinate, <i>S</i>-(2-hydroxylethyl) phenylmethanethiosulfinate, <i>S</i>-benzyl 2-hydroxyethane)thiosulfinate and <i>S</i>-benzyl phenylmethanethiosulfinate (petivericin; PhCH<sub>2</sub>S(O)SCH<sub>2</sub>Ph).<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> Asparagusic acid <i>S</i>-oxide<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> and brugierol<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> are other natural 1,2-dithiolane-1-oxides occurring in <i><a href="/wiki/Asparagus_officinalis" class="mw-redirect" title="Asparagus officinalis">Asparagus officinalis</a></i> and <i><a href="/wiki/Bruguiera_conjugata" class="mw-redirect" title="Bruguiera conjugata">Bruguiera conjugata</a></i>, respectively. </p> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thiosulfinate&action=edit&section=2" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Allicin, <i>S</i>-benzyl phenylmethanethiosulfinate, and related thiosulfinates show radical-trapping <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> activity associated with easy formation of sulfenic acids<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> The acyclic thiosulfinates from <i>Allium</i> and <i>Brassica</i> species possess antimicrobial, antiparasitic, antitumor and cysteine protease inhibitory activity while the natural 1,2-dithiolane-1-oxides are growth inhibitors. The thiosulfinates from <i>Petiveria</i> also exhibit antimicrobial activity.<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> </p><p>Thiosulfinates feature a S(IV) center linked to a S(II) center, the former being <a href="/wiki/Stereogenic" class="mw-redirect" title="Stereogenic">stereogenic</a>. Conversion of simple disulfides to thiosulfinates results in a considerable weakening of the S–S bond from about 47.8 to 28.0 kcal mol<sup>−1</sup> for the S-S bond in PhS(O)SPh and from about 63.2 to 39.3 kcal mol<sup>−1</sup> for the S-S bond in MeS(O)SMe,<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> with the consequence that most thiosulfinates are both unstable and quite reactive. For this reason the mixtures of thiosulfinates from <i>Allium</i> plants can best be separated by <a href="/wiki/HPLC" class="mw-redirect" title="HPLC">HPLC</a> at room temperature rather than by <a href="/wiki/Gas_chromatography" title="Gas chromatography">gas chromatography</a> (GC), although GC has been used with some low molecular weight thiosulfinates. Thiosulfinates can be distinguished from <a href="/wiki/Sulfoxide" title="Sulfoxide">sulfoxides</a> by <a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">infrared spectroscopy</a> since they have a characteristic S=O band at about 1078 cm<sup>−1</sup> compared to 1030–1060 cm<sup>−1</sup> in sulfoxides.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Formation_and_reactions">Formation and reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thiosulfinate&action=edit&section=3" title="Edit section: Formation and reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Synthetic thiosulfinates were first reported in 1947 by Cavallito and coworkers by <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of the corresponding disulfides.<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> </p><p>One example of a moderately stable thiosulfinate is the <i>tert</i>-<a href="/wiki/Butyl" class="mw-redirect" title="Butyl">butyl</a> derivative, (CH<sub>3</sub>)<sub>3</sub>CS(O)SC(CH<sub>3</sub>)<sub>3</sub>. This thiosulfinate can be obtained in optical purity by catalytic <a href="/wiki/Asymmetric_catalytic_oxidation" title="Asymmetric catalytic oxidation">asymmetric oxidation</a> of di-<i>tert</i>-butyl disulfide with <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Upon heating, (CH<sub>3</sub>)<sub>3</sub>CS(O)SC(CH<sub>3</sub>)<sub>3</sub> decomposes into <i>tert</i>-butanethiosulfoxylic acid (CH<sub>3</sub>)<sub>3</sub>CSSOH) as shown by trapping studies.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>In a similar manner racemic methyl methanethiosulfinate (CH<sub>3</sub>S(O)SCH<sub>3</sub>) can be obtained by <a href="/wiki/Peracetic_acid" title="Peracetic acid">peracetic acid</a> oxidation of <a href="/wiki/Dimethyl_disulfide" title="Dimethyl disulfide">dimethyl disulfide</a>.<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> Methyl methanethiosulfinate decomposes thermally giving methanesulfenic acid (CH<sub>3</sub>SOH), the simplest <a href="/wiki/Sulfenic_acid" title="Sulfenic acid">sulfenic acid</a>, as well as <a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">thioformaldehyde</a> (CH<sub>2</sub>=S). Methyl methanethiosulfinate can also disproportionate to a 1:1 mixture of dimethyl disulfide and methyl methanethiosulfonate (CH<sub>3</sub>SO<sub>2</sub>SCH<sub>3</sub>) and rearrange via a <a href="/wiki/Pummerer_rearrangement" title="Pummerer rearrangement">Pummerer rearrangement</a> to CH<sub>3</sub>S(O)CH<sub>2</sub>SSCH<sub>3</sub>.<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><p>An unusual three-membered ring thiosulfinate (a dithiirane 1-oxide) has been prepared through rearrangement of a 1,3-<a href="/wiki/Dithietane" title="Dithietane">dithietane</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> A related compound, 3-(9-triptycyl)dithiirane-1-oxide, was prepared by the reaction of (9-triptycyl)diazomethane and <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"><a href="/wiki/S8O" class="mw-redirect" title="S8O">S<sub class="template-chem2-sub">8</sub>O</a></span>. The <a href="/wiki/X-ray_structure" class="mw-redirect" title="X-ray structure">X-ray structure</a> of the dithiirane-1-oxide reveals a significantly lengthened sulfur-sulfur bond (211.9(3)pm).<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>Thiosulfinates have also been invoked as intermediates in the oxidation of <a href="/wiki/Thiol" title="Thiol">thiols</a> to <a href="/wiki/Sulfonic_acid" title="Sulfonic acid">sulfonic acids</a>. </p> <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=Thiosulfinate&action=edit&section=4" 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 .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text">See <a href="/wiki/Sulfoxide" title="Sulfoxide">sulfoxide</a> for discussion and references regarding the bonding in divalent monooxosulfur structures.</span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><style 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="CITEREFBlockWeidner1966" class="citation journal cs1">Block, S. S.; Weidner, J. P. (1966) [1 Sept 1964]. "Vibrational behavior and structure of disulfide dioxides (thiolsulfonates)". <i>Applied Spectroscopy</i>. <b>20</b> (2): <span class="nowrap">73–</span>79. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1966ApSpe..20...73B">1966ApSpe..20...73B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1366%2F000370266774386272">10.1366/000370266774386272</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Applied+Spectroscopy&rft.atitle=Vibrational+behavior+and+structure+of+disulfide+dioxides+%28thiolsulfonates%29&rft.volume=20&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E73-%3C%2Fspan%3E79&rft.date=1966&rft_id=info%3Adoi%2F10.1366%2F000370266774386272&rft_id=info%3Abibcode%2F1966ApSpe..20...73B&rft.aulast=Block&rft.aufirst=S.+S.&rft.au=Weidner%2C+J.+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKice_JL1980" class="citation journal cs1">Kice JL (1980). "Mechanisms and reactivity in reactions of organic oxyacids of sulfur and their anhydrides". <i>Advances in Physical Organic Chemistry</i>. <b>17</b>: <span class="nowrap">65–</span>181. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0065-3160%2808%2960128-8">10.1016/S0065-3160(08)60128-8</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780120335176" title="Special:BookSources/9780120335176"><bdi>9780120335176</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Advances+in+Physical+Organic+Chemistry&rft.atitle=Mechanisms+and+reactivity+in+reactions+of+organic+oxyacids+of+sulfur+and+their+anhydrides&rft.volume=17&rft.pages=%3Cspan+class%3D%22nowrap%22%3E65-%3C%2Fspan%3E181&rft.date=1980&rft_id=info%3Adoi%2F10.1016%2FS0065-3160%2808%2960128-8&rft.isbn=9780120335176&rft.au=Kice+JL&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTakataEndo,_T1990" class="citation book cs1">Takata, T; Endo, T (1990). "Thiosulphinic acids and esters". In S. Patai (ed.). <i>The Chemistry of Sulphinic Acids, Esters and Their Derivatives</i>. New York: John Wiley. pp. <span class="nowrap">527–</span>575. <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%2F9780470772270.ch18">10.1002/9780470772270.ch18</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470772270" title="Special:BookSources/9780470772270"><bdi>9780470772270</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Thiosulphinic+acids+and+esters&rft.btitle=The+Chemistry+of+Sulphinic+Acids%2C+Esters+and+Their+Derivatives&rft.place=New+York&rft.pages=%3Cspan+class%3D%22nowrap%22%3E527-%3C%2Fspan%3E575&rft.pub=John+Wiley&rft.date=1990&rft_id=info%3Adoi%2F10.1002%2F9780470772270.ch18&rft.isbn=9780470772270&rft.aulast=Takata&rft.aufirst=T&rft.au=Endo%2C+T&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBravermanCherkinsky,_M.Levinger,_S.2007" class="citation journal cs1">Braverman, S; Cherkinsky, M.; Levinger, S. (2007). "Alkanethiosulfinic Acid Esters". <i>Sci. Synth</i>. <b>39</b>: <span class="nowrap">229–</span>235.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Sci.+Synth.&rft.atitle=Alkanethiosulfinic+Acid+Esters&rft.volume=39&rft.pages=%3Cspan+class%3D%22nowrap%22%3E229-%3C%2Fspan%3E235&rft.date=2007&rft.aulast=Braverman&rft.aufirst=S&rft.au=Cherkinsky%2C+M.&rft.au=Levinger%2C+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKubecCody,_RBDane,_AJMusah,_RA2010" class="citation journal cs1">Kubec, R; Cody, RB; Dane, AJ; Musah, RA; Schraml, J; Vattekkatte, A; Block, E (2010). "Applications of DART Mass Spectrometry in <i>Allium</i> Chemistry. (<i>Z</i>)-Butanethial <i>S</i>-Oxide and 1-Butenyl Thiosulfinates and their <i>S</i>-(<i>E</i>)-1-Butenylcysteine <i>S</i>-Oxide Precursor from <i>Allium siculum</i>". <i>J. Agric. Food Chem</i>. <b>58</b> (2): <span class="nowrap">1121–</span>1128. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjf903733e">10.1021/jf903733e</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/20047275">20047275</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Agric.+Food+Chem.&rft.atitle=Applications+of+DART+Mass+Spectrometry+in+Allium+Chemistry.+%28Z%29-Butanethial+S-Oxide+and+1-Butenyl+Thiosulfinates+and+their+S-%28E%29-1-Butenylcysteine+S-Oxide+Precursor+from+Allium+siculum&rft.volume=58&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1121-%3C%2Fspan%3E1128&rft.date=2010&rft_id=info%3Adoi%2F10.1021%2Fjf903733e&rft_id=info%3Apmid%2F20047275&rft.aulast=Kubec&rft.aufirst=R&rft.au=Cody%2C+RB&rft.au=Dane%2C+AJ&rft.au=Musah%2C+RA&rft.au=Schraml%2C+J&rft.au=Vattekkatte%2C+A&rft.au=Block%2C+E&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlockDane,_AJThomas,_SCody,_RB2010" class="citation journal cs1">Block, E; Dane, AJ; Thomas, S; Cody, RB (2010). "Applications of Direct Analysis in Real Time–Mass Spectrometry (DART-MS) in <i>Allium</i> Chemistry. 2-Propenesulfenic and 2-Propenesulfinic Acids, Diallyl Trisulfane <i>S</i>-Oxide and Other Reactive Sulfur Compounds from Crushed Garlic and Other Alliums". <i>J. Agric. Food Chem</i>. <b>58</b> (8): <span class="nowrap">4617–</span>4625. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2010JAFC...58.4617B">2010JAFC...58.4617B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjf1000106">10.1021/jf1000106</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/20225897">20225897</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Agric.+Food+Chem.&rft.atitle=Applications+of+Direct+Analysis+in+Real+Time%E2%80%93Mass+Spectrometry+%28DART-MS%29+in+Allium+Chemistry.+2-Propenesulfenic+and+2-Propenesulfinic+Acids%2C+Diallyl+Trisulfane+S-Oxide+and+Other+Reactive+Sulfur+Compounds+from+Crushed+Garlic+and+Other+Alliums&rft.volume=58&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E4617-%3C%2Fspan%3E4625&rft.date=2010&rft_id=info%3Apmid%2F20225897&rft_id=info%3Adoi%2F10.1021%2Fjf1000106&rft_id=info%3Abibcode%2F2010JAFC...58.4617B&rft.aulast=Block&rft.aufirst=E&rft.au=Dane%2C+AJ&rft.au=Thomas%2C+S&rft.au=Cody%2C+RB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHiraiSakashita,_SSano,_TInoue,_T2000" class="citation journal cs1">Hirai, N; Sakashita, S; Sano, T; Inoue, T; Ohigashi, H; Premasthira, C; Asakawa, Y; Harada, J; Fujii, Y (2000). "Allelochemicals of the tropical weed <i>Sphenoclea zeylanica</i>". <i>Phytochemistry</i>. <b>55</b> (2): <span class="nowrap">131–</span>140. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2000PChem..55..131H">2000PChem..55..131H</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0031-9422%2800%2900264-8">10.1016/S0031-9422(00)00264-8</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/11065289">11065289</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Phytochemistry&rft.atitle=Allelochemicals+of+the+tropical+weed+Sphenoclea+zeylanica&rft.volume=55&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E131-%3C%2Fspan%3E140&rft.date=2000&rft_id=info%3Apmid%2F11065289&rft_id=info%3Adoi%2F10.1016%2FS0031-9422%2800%2900264-8&rft_id=info%3Abibcode%2F2000PChem..55..131H&rft.aulast=Hirai&rft.aufirst=N&rft.au=Sakashita%2C+S&rft.au=Sano%2C+T&rft.au=Inoue%2C+T&rft.au=Ohigashi%2C+H&rft.au=Premasthira%2C+C&rft.au=Asakawa%2C+Y&rft.au=Harada%2C+J&rft.au=Fujii%2C+Y&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKubecKim,_SMusah,_RA2002" class="citation journal cs1">Kubec, R; Kim, S; Musah, RA (2002). <a rel="nofollow" class="external text" href="http://www.rabimusah.com/pdfs/Cysteine%20S-Substituted%20Cysteine%20Derivatives_part%202.pdf">"S-Substituted cysteine derivatives and thiosulfinate formation in Petiveria alliacea--Part II"</a> <span class="cs1-format">(PDF)</span>. <i>Phytochemistry</i>. <b>61</b> (6): <span class="nowrap">675–</span>680. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2002PChem..61..675K">2002PChem..61..675K</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0031-9422%2802%2900328-X">10.1016/S0031-9422(02)00328-X</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/12423888">12423888</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Phytochemistry&rft.atitle=S-Substituted+cysteine+derivatives+and+thiosulfinate+formation+in+Petiveria+alliacea--Part+II&rft.volume=61&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E675-%3C%2Fspan%3E680&rft.date=2002&rft_id=info%3Apmid%2F12423888&rft_id=info%3Adoi%2F10.1016%2FS0031-9422%2802%2900328-X&rft_id=info%3Abibcode%2F2002PChem..61..675K&rft.aulast=Kubec&rft.aufirst=R&rft.au=Kim%2C+S&rft.au=Musah%2C+RA&rft_id=http%3A%2F%2Fwww.rabimusah.com%2Fpdfs%2FCysteine%2520S-Substituted%2520Cysteine%2520Derivatives_part%25202.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYanagawaKato,_TKitahara,_Y1973" class="citation journal cs1">Yanagawa, H; Kato, T; Kitahara, Y (1973). "Asparagusic acid-<i>S</i>-oxides, new plant growth regulators in etiolated young asparagus shoots". <i>Tetrahedron Letters</i>. <b>14</b> (13): <span class="nowrap">1073–</span>1075. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0040-4039%2801%2995907-6">10.1016/S0040-4039(01)95907-6</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Letters&rft.atitle=Asparagusic+acid-S-oxides%2C+new+plant+growth+regulators+in+etiolated+young+asparagus+shoots&rft.volume=14&rft.issue=13&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1073-%3C%2Fspan%3E1075&rft.date=1973&rft_id=info%3Adoi%2F10.1016%2FS0040-4039%2801%2995907-6&rft.aulast=Yanagawa&rft.aufirst=H&rft.au=Kato%2C+T&rft.au=Kitahara%2C+Y&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKatoNumata_M1972" class="citation journal cs1">Kato, A; Numata M (1972). "Brugierol and isobrugierol, <i>trans</i>- and <i>cis</i>-1,2-dithiolane-1-oxide, from <i>Brugiera conjugata</i>". <i>Tetrahedron Letters</i>. <b>13</b> (3): <span class="nowrap">203–</span>206. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0040-4039%2801%2984280-5">10.1016/S0040-4039(01)84280-5</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Letters&rft.atitle=Brugierol+and+isobrugierol%2C+trans-+and+cis-1%2C2-dithiolane-1-oxide%2C+from+Brugiera+conjugata&rft.volume=13&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E203-%3C%2Fspan%3E206&rft.date=1972&rft_id=info%3Adoi%2F10.1016%2FS0040-4039%2801%2984280-5&rft.aulast=Kato&rft.aufirst=A&rft.au=Numata+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLynettButts,_KVaidya,_VGarretta,_GE2011" class="citation journal cs1">Lynett, PT; Butts, K; Vaidya, V; Garretta, GE; Pratt, DA (2011). "The mechanism of radical-trapping antioxidant activity of plant-derived thiosulfinates". <i>Org. Biomol. Chem</i>. <b>9</b> (9): <span class="nowrap">3320–</span>3330. <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%2Fc1ob05192j">10.1039/c1ob05192j</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/21445384">21445384</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Org.+Biomol.+Chem.&rft.atitle=The+mechanism+of+radical-trapping+antioxidant+activity+of+plant-derived+thiosulfinates&rft.volume=9&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3320-%3C%2Fspan%3E3330&rft.date=2011&rft_id=info%3Adoi%2F10.1039%2Fc1ob05192j&rft_id=info%3Apmid%2F21445384&rft.aulast=Lynett&rft.aufirst=PT&rft.au=Butts%2C+K&rft.au=Vaidya%2C+V&rft.au=Garretta%2C+GE&rft.au=Pratt%2C+DA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKimKubec,_RMusah,_RA2006" class="citation journal cs1">Kim, S; Kubec, R; Musah, RA (2006). <a rel="nofollow" class="external text" href="http://www.rabimusah.com/pdfs/Antibacterial%20and%20Antifungal%20Activity.pdf">"Antibacterial and antifungal activity of sulfur-containing compounds from Petiveria alliacea"</a> <span class="cs1-format">(PDF)</span>. <i>Journal of Ethnopharmacology</i>. <b>104</b> (<span class="nowrap">1–</span>2): <span class="nowrap">188–</span>192. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.jep.2005.08.072">10.1016/j.jep.2005.08.072</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/16229980">16229980</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Ethnopharmacology&rft.atitle=Antibacterial+and+antifungal+activity+of+sulfur-containing+compounds+from+Petiveria+alliacea&rft.volume=104&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E188-%3C%2Fspan%3E192&rft.date=2006&rft_id=info%3Adoi%2F10.1016%2Fj.jep.2005.08.072&rft_id=info%3Apmid%2F16229980&rft.aulast=Kim&rft.aufirst=S&rft.au=Kubec%2C+R&rft.au=Musah%2C+RA&rft_id=http%3A%2F%2Fwww.rabimusah.com%2Fpdfs%2FAntibacterial%2520and%2520Antifungal%2520Activity.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlockCotelesageDikarevGarosi2024" class="citation journal cs1">Block, E.; Cotelesage, J.J.H.; Dikarev, E.; Garosi, B.; George, G.N.; Musah, R.A.; Vogt, L.I.; Wei, Z.; Zhang, Y. (2024). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11574841">"Re-examination of the claimed isolation of stable noncyclic 1,2-disulfoxides"</a>. <i>Organic Letters</i>. <b>26</b> (45): <span class="nowrap">9619–</span>9624. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.orglett.4c02849">10.1021/acs.orglett.4c02849</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11574841">11574841</a></span>. <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/39230394">39230394</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Letters&rft.atitle=Re-examination+of+the+claimed+isolation+of+stable+noncyclic+1%2C2-disulfoxides&rft.volume=26&rft.issue=45&rft.pages=%3Cspan+class%3D%22nowrap%22%3E9619-%3C%2Fspan%3E9624&rft.date=2024&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11574841%23id-name%3DPMC&rft_id=info%3Apmid%2F39230394&rft_id=info%3Adoi%2F10.1021%2Facs.orglett.4c02849&rft.aulast=Block&rft.aufirst=E.&rft.au=Cotelesage%2C+J.J.H.&rft.au=Dikarev%2C+E.&rft.au=Garosi%2C+B.&rft.au=George%2C+G.N.&rft.au=Musah%2C+R.A.&rft.au=Vogt%2C+L.I.&rft.au=Wei%2C+Z.&rft.au=Zhang%2C+Y.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11574841&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlock_E2010" class="citation book cs1">Block E (2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=6AB89RHV9ucC"><i>Garlic and Other Alliums: The Lore and the Science</i></a>. Royal Society of Chemistry. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-190-9" title="Special:BookSources/978-0-85404-190-9"><bdi>978-0-85404-190-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Garlic+and+Other+Alliums%3A+The+Lore+and+the+Science&rft.pub=Royal+Society+of+Chemistry&rft.date=2010&rft.isbn=978-0-85404-190-9&rft.au=Block+E&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D6AB89RHV9ucC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></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="CITEREFSmallBailey,_JHCavallito,_CJ1947" class="citation journal cs1">Small, LD; Bailey, JH; Cavallito, CJ (1947). "Alkyl thiolsulfinates". <i>J. Am. Chem. Soc</i>. <b>69</b> (7): <span class="nowrap">1710–</span>1713. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1947JAChS..69.1710S">1947JAChS..69.1710S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01199a040">10.1021/ja01199a040</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/20251406">20251406</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Alkyl+thiolsulfinates&rft.volume=69&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1710-%3C%2Fspan%3E1713&rft.date=1947&rft_id=info%3Apmid%2F20251406&rft_id=info%3Adoi%2F10.1021%2Fja01199a040&rft_id=info%3Abibcode%2F1947JAChS..69.1710S&rft.aulast=Small&rft.aufirst=LD&rft.au=Bailey%2C+JH&rft.au=Cavallito%2C+CJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWeixEllman,_JA2005" class="citation journal cs1">Weix, DJ; Ellman, JA (2005). "(RS)-(+)-2-Methyl-2-Propanesulfinamide [<i>tert</i>-Butanesulfinamide]". <i>Organic Syntheses</i>. <b>82</b>: 157. <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%2F0471264229.os082.24">10.1002/0471264229.os082.24</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=%28RS%29-%28%2B%29-2-Methyl-2-Propanesulfinamide+%5Btert-Butanesulfinamide%5D&rft.volume=82&rft.pages=157&rft.date=2005&rft_id=info%3Adoi%2F10.1002%2F0471264229.os082.24&rft.aulast=Weix&rft.aufirst=DJ&rft.au=Ellman%2C+JA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlock1972" class="citation journal cs1">Block, E (1972). "The Chemistry of Alkyl Thiosulfinate Esters. III. tert-Butanethiosulfoxylic Acid". <i>J. Am. Chem. Soc</i>. <b>94</b> (2): <span class="nowrap">644–</span>645. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1972JAChS..94..644B">1972JAChS..94..644B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00757a060">10.1021/ja00757a060</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=The+Chemistry+of+Alkyl+Thiosulfinate+Esters.+III.+tert-Butanethiosulfoxylic+Acid&rft.volume=94&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E644-%3C%2Fspan%3E645&rft.date=1972&rft_id=info%3Adoi%2F10.1021%2Fja00757a060&rft_id=info%3Abibcode%2F1972JAChS..94..644B&rft.aulast=Block&rft.aufirst=E&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMooreO'Connor,_DE1966" class="citation journal cs1">Moore, TL; O'Connor, DE (1966). "The Reaction of Methanesulfenyl Chloride with Alkoxides and Alcohols. Preparation of Aliphatic Sulfenate and Sulfinate Esters". <i>J. Org. Chem</i>. <b>31</b> (11): <span class="nowrap">3587–</span>3592. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo01349a027">10.1021/jo01349a027</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Org.+Chem.&rft.atitle=The+Reaction+of+Methanesulfenyl+Chloride+with+Alkoxides+and+Alcohols.+Preparation+of+Aliphatic+Sulfenate+and+Sulfinate+Esters&rft.volume=31&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3587-%3C%2Fspan%3E3592&rft.date=1966&rft_id=info%3Adoi%2F10.1021%2Fjo01349a027&rft.aulast=Moore&rft.aufirst=TL&rft.au=O%27Connor%2C+DE&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlockO'Connor,_J1974" class="citation journal cs1">Block, E; O'Connor, J (1974). "The Chemistry of Alkyl Thiosulfinate Esters. VI. Preparation and Spectral Studies". <i>J. Am. Chem. Soc</i>. <b>96</b> (12): <span class="nowrap">3921–</span>3929. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1974JAChS..96.3921B">1974JAChS..96.3921B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00819a033">10.1021/ja00819a033</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=The+Chemistry+of+Alkyl+Thiosulfinate+Esters.+VI.+Preparation+and+Spectral+Studies&rft.volume=96&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3921-%3C%2Fspan%3E3929&rft.date=1974&rft_id=info%3Adoi%2F10.1021%2Fja00819a033&rft_id=info%3Abibcode%2F1974JAChS..96.3921B&rft.aulast=Block&rft.aufirst=E&rft.au=O%27Connor%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlockO'Connor,_J1974" class="citation journal cs1">Block, E; O'Connor, J (1974). "The Chemistry of Alkyl Thiosulfinate Esters. VII. Mechanistic Studies and Synthetic Applications". <i>J. Am. Chem. Soc</i>. <b>96</b> (12): <span class="nowrap">3929–</span>3944. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1974JAChS..96.3929B">1974JAChS..96.3929B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00819a034">10.1021/ja00819a034</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=The+Chemistry+of+Alkyl+Thiosulfinate+Esters.+VII.+Mechanistic+Studies+and+Synthetic+Applications&rft.volume=96&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3929-%3C%2Fspan%3E3944&rft.date=1974&rft_id=info%3Adoi%2F10.1021%2Fja00819a034&rft_id=info%3Abibcode%2F1974JAChS..96.3929B&rft.aulast=Block&rft.aufirst=E&rft.au=O%27Connor%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIshiiAkazawa,_TDing,_MXHonjo,_T1993" class="citation journal cs1">Ishii, A; Akazawa, T; Ding, MX; Honjo, T; Nakayama, J; Hoshino, M; Shiro, M (1993). "First isolable dithiiranes: 3-(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-3-phenyldithiirane 1-oxides". <i>J. Am. Chem. Soc</i>. <b>115</b> (11): <span class="nowrap">4914–</span>4915. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1993JAChS.115.4914I">1993JAChS.115.4914I</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00064a072">10.1021/ja00064a072</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=First+isolable+dithiiranes%3A+3-%281%2C1%2C3%2C3-tetramethyl-4-oxo-4-phenylbutyl%29-3-phenyldithiirane+1-oxides&rft.volume=115&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E4914-%3C%2Fspan%3E4915&rft.date=1993&rft_id=info%3Adoi%2F10.1021%2Fja00064a072&rft_id=info%3Abibcode%2F1993JAChS.115.4914I&rft.aulast=Ishii&rft.aufirst=A&rft.au=Akazawa%2C+T&rft.au=Ding%2C+MX&rft.au=Honjo%2C+T&rft.au=Nakayama%2C+J&rft.au=Hoshino%2C+M&rft.au=Shiro%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIshiiKawai,_TNoji,_MNakayama,_J2005" class="citation journal cs1">Ishii, A; Kawai, T; Noji, M; Nakayama, J (2005). "Synthesis and reactions of a monosubstituted dithiirane 1-oxide, 3-(9-triptycyl)dithiirane 1-oxide". <i>Tetrahedron</i>. <b>61</b> (28): <span class="nowrap">6693–</span>6699. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.tet.2005.05.017">10.1016/j.tet.2005.05.017</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron&rft.atitle=Synthesis+and+reactions+of+a+monosubstituted+dithiirane+1-oxide%2C+3-%289-triptycyl%29dithiirane+1-oxide&rft.volume=61&rft.issue=28&rft.pages=%3Cspan+class%3D%22nowrap%22%3E6693-%3C%2Fspan%3E6699&rft.date=2005&rft_id=info%3Adoi%2F10.1016%2Fj.tet.2005.05.017&rft.aulast=Ishii&rft.aufirst=A&rft.au=Kawai%2C+T&rft.au=Noji%2C+M&rft.au=Nakayama%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThiosulfinate" class="Z3988"></span></span> </li> </ol></div></div> <div 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group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silicon" title="Silicon">Silicon</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Silane" title="Silane">Silane</a> <ul><li><a href="/wiki/Hydrosilane" class="mw-redirect" title="Hydrosilane">Hydrosilane</a></li> <li><a href="/wiki/Chlorosilane" title="Chlorosilane">Chlorosilane</a></li></ul></li> <li><a href="/wiki/Organosilicon_chemistry#Silenes" title="Organosilicon chemistry">Silene</a></li> <li><a href="/wiki/Silanol" title="Silanol">Silanol</a></li> <li><a href="/wiki/Siloxide" title="Siloxide">Siloxide</a></li> <li><a href="/wiki/Siloxane" title="Siloxane">Siloxane</a></li> <li><a href="/wiki/Silanone" title="Silanone">Silanone</a></li> <li><a href="/wiki/Silyl_ether" title="Silyl ether">Silether</a></li> <li><a href="/wiki/Metalloles" class="mw-redirect" title="Metalloles">Silole</a></li> <li><a href="/wiki/Silatrane" class="mw-redirect" title="Silatrane">Silatrane</a></li> <li><a href="/wiki/Silicate" title="Silicate">Silicate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Thioether" class="mw-redirect" title="Thioether">Thioether</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a class="mw-selflink selflink">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li> <li><a href="/wiki/Selenide#Inorganic_selenides" title="Selenide">Selenoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li> <li><a href="/wiki/Telluride_(chemistry)#Organic_tellurides" title="Telluride (chemistry)">telluroether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polonium" title="Polonium">Polonium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Polonium_hydride#Properties" title="Polonium hydride">Polonol</a></li> <li><a href="/wiki/Organopolonium_chemistry" title="Organopolonium chemistry">Polonoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div>    </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=Thiosulfinate&oldid=1275148035">https://en.wikipedia.org/w/index.php?title=Thiosulfinate&oldid=1275148035</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div 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