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Sulfilimine
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<h2 id="preparation">Preparation</h2> <p>Most sulfilimines are <i>N</i>-substituted with electron-withdrawing groups. These compounds are typically prepared by oxidation of thioethers with electrophilic amine reagents, such as <a href="/facts/Chloramine-T/kcF2SMX7">chloramine-T</a> in the presence of a base:<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> </p> R2S + ClNHTs → R2S=NTs + HCl <p>An alternative route involves reactions of electrophilic sulfur compounds with amines. The imidosulfonium reagents provide a source of "Me2S2+", which are attacked by amines. </p><p>In general, aliphatic sulfilimines are not stable above −30 °C (−22 °F).<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> </p><p><a href="/facts/Potassium_permanganate/nyjjuDlo">KMnO4</a> can oxidize sulfilimines to sulfoximines, but the latter are more generally produced from addition of <a href="/facts/Azide/AaJwyv1z">azides</a> to <a href="/facts/Sulfoxide/Stk3Vnj9">sulfoxides</a>.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p> <h2 id="sulfilimine-bonds-in-proteins">Sulfilimine bonds in proteins</h2> <p>Sulfilimine bonds stabilize <a href="/facts/Type-IV_collagen/v6JPysy9">collagen IV</a> strands found in the <a href="/facts/Extracellular_matrix/kaHC5Ez8">extracellular matrix</a><a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> and arose at least 500 mya.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> These bonds covalently connect <a href="/facts/Hydroxylysine/tdVRJ9IV">hydroxylysine</a> and <a href="/facts/Methionine/7neydPKo">methionine</a> residues of adjacent polypeptide strands to form a larger collagen trimer. </p> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>"S,S-Diphenylsulfilimine". Sigma-Aldrich. <a href="https://www.sigmaaldrich.com/catalog/product/aldrich/232173" target="_blank">https://www.sigmaaldrich.com/catalog/product/aldrich/232173</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>"(R)-(−)-S-Methyl-S-phenylsulfoximine". Sigma-Aldrich. <a href="https://www.sigmaaldrich.com/catalog/product/aldrich/68916" target="_blank">https://www.sigmaaldrich.com/catalog/product/aldrich/68916</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Gilchrist, Thomas L.; Moody, Christopher J. (1977). "The chemistry of sulfilimines". Chemical Reviews. 77 (3): 409–435. doi:10.1021/cr60307a005. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Roesky, H. W. (1971). "The Sulfur–Nitrogen Bond". In Senning, Alexander (ed.). Sulfur in Organic and Inorganic Chemistry. Vol. 1. New York: Marcel Dekker. pp. 27–28, 30–31. ISBN 0-8247-1615-9. LCCN 70-154612. <a href="0-8247-1615-9" target="_blank">0-8247-1615-9</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Roesky, H. W. (1971). "The Sulfur–Nitrogen Bond". In Senning, Alexander (ed.). Sulfur in Organic and Inorganic Chemistry. Vol. 1. New York: Marcel Dekker. pp. 27–28, 30–31. ISBN 0-8247-1615-9. LCCN 70-154612. <a href="0-8247-1615-9" target="_blank">0-8247-1615-9</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Vanacore R, Ham AL, Voehler M, Sanders CR, Conrads TP, Veenstra TD, Sharpless KB, Dawson PE, Hudson BG (September 4, 2009). "A sulfilimine bond identified in collagen IV". Science. 325 (5945): 1230–1234. Bibcode:2009Sci...325.1230V. doi:10.1126/science.1176811. PMC 2876822. PMID 19729652. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2876822" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2876822</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Fidler, Aaron L.; Vanacore, Roberto M.; Chetyrkin, Sergei V.; Pedchenko, Vadim K.; Bhave, Gautam; Yin, Viravuth P.; Stothers, Cody L.; Rose, Kristie Lindsey; McDonald, W. Hayes; Clark, Travis A.; Borza, Dorin-Bogdan; Steele, Robert E.; Ivy, Michael T.; Hudson, Julie K.; Hudson, Billy G.; Hudson, Billy G. (2014). "A unique covalent bond in basement membrane is a primordial innovation for tissue evolution". Proceedings of the National Academy of Sciences. 111 (1): 331–336. Bibcode:2014PNAS..111..331F. doi:10.1073/pnas.1318499111. PMC 3890831. PMID 24344311. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3890831" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3890831</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> </ol>