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Furoin or 1,2-di(furan-2-yl)-2-hydroxyethanone is an organic compound with formula C10H8O4. It can be produced from furfural by a benzoin condensation reaction catalyized by cyanide ions.
Contents
Reactions
Furoin synthesis from furfural is also catalyzed by vitamin B1 (thiamine). In 1957, R. Breslow proposed that this reaction involves a relatively stable carbene form of thiamine: In the catalytic cycle shown below two molecules of furfural react to give furoin, via a thiazol-2-ylidene catalyst, resulting from loss of one proton at carbon 2 of the thiazolium cation of vitamin B1:
This was the first evidence for the existence of persistent carbenes.
Uses
Furoin has been used as a plasticizer.
References
Furoin Wikipedia(Text) CC BY-SA