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Paper | Regular issue | Vol 71, No. 4, 2007, pp.903-910
Published online, 21st February, 2007
DOI: 10.3987/COM-07-11002
Mechanism of Criss-Cross Reaction of Aromatic Glyoxalimines with Potassium Cyanate and Thiocyanate

Jirí Hanusek,* Jirí Verner, and Milan Potácek

*University of Pardubice, Department of Organic Chemistry, Nám. Cs. legií 565, CZ-532 10 Pardubice, Czech Republic


Aromatic 1,4-diazabuta-1,3-dienes (glyoxalimines) react with potassium cyanate and thiocyanate in ethereal acetic acid to give the corresponding4-acetoxy-5-(4-substituted phenylamino)-3-(4-substituted phenyl)- imidazolidin-2-ones and perhydroimidazo[4,5-d]imidazol-2,5-dithiones, respectively. In order to learn more about the reaction mechanism, kinetic measurements have been carried out. It was found that the reaction involves a direct nucleophilic addition of thiocyanate anion to 1,4-diazabuta-1,3-diene, whereas the less nucleophilic cyanate anion requires acid catalysis.