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Furoin
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<h2 id="reactions">Reactions</h2> <p>Furoin synthesis from furfural is also catalyzed by <a href="/facts/Vitamin_B1/37RC4MCS">vitamin B1</a> (thiamine). In 1957, <a href="/facts/Ronald_Breslow/1PNH70wj">Ronald Breslow</a> proposed that this reaction involves a relatively stable <a href="/facts/Carbene/3WxNSStY">carbene</a> form of thiamine.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a><a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> In the <a href="/facts/Catalytic_cycle/At7x3sNe">catalytic cycle</a> shown below two <a href="/facts/Molecules/N9ljSfFq">molecules</a> of furfural react to give furoin, via a thiazol-2-ylidene <a href="/facts/Catalyst/LPBS7TQC">catalyst</a>, resulting from loss of one <a href="/facts/Proton/clCjepXP">proton</a> at carbon 2 of the <a href="/facts/Thiazolium_salt/xtUANXCR">thiazolium</a> <a href="/facts/Cation/wrbwhF3z">cation</a> of vitamin B1: </p> <p>This was the first evidence for the existence of <a href="/facts/Persistent_carbene/g4U9YPae">persistent carbenes</a>. </p> <h2 id="uses">Uses</h2> <p>Furoin has been used as a <a href="/facts/Plasticizer/RjzuplRY">plasticizer</a>.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> </p> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Denis Lorient (1999), New ingredients in food processing: biochemistry and agriculture. Woodhead Publishing ISBN 1-85573-443-5 366 pages <a href="https://books.google.com/books?id=EnPMWNp4-L0C&dq=furoin" target="_blank">https://books.google.com/books?id=EnPMWNp4-L0C&dq=furoin</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Ronald Breslow (1957). "Mechanism of Thiamine Action: Participation of a Thiazolium Zwitterion". Chemistry and Industry. 26: 893. <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>R. Breslow (1957). "Rapid Deuterium Exchange in Thiazolium Salts". Journal of the American Chemical Society. 79 (7): 1762–1763. doi:10.1021/ja01564a064. <a href="/wiki/Journal_of_the_American_Chemical_Society" target="_blank">/wiki/Journal_of_the_American_Chemical_Society</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Denis Lorient (1999), New ingredients in food processing: biochemistry and agriculture. Woodhead Publishing ISBN 1-85573-443-5 366 pages <a href="https://books.google.com/books?id=EnPMWNp4-L0C&dq=furoin" target="_blank">https://books.google.com/books?id=EnPMWNp4-L0C&dq=furoin</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> </ol>