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 catalyzed by cyanide ions.[1]
Reactions
Furoin synthesis from furfural is also catalyzed by vitamin B1 (thiamine). In 1957, Ronald Breslow proposed that this reaction involves a relatively stable carbene form of thiamine.[2][3] 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.[1]
References
- ^ a b Denis Lorient (1999), New ingredients in food processing: biochemistry and agriculture. Woodhead Publishing ISBN 1-85573-443-5 366 pages
- ^ Ronald Breslow (1957). "Mechanism of Thiamine Action: Participation of a Thiazolium Zwitterion". Chemistry and Industry. 26: 893.
- ^ R. Breslow (1957). "Rapid Deuterium Exchange in Thiazolium Salts". Journal of the American Chemical Society. 79 (7): 1762–1763. doi:10.1021/ja01564a064.