HETEROCYCLES

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

■ 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

Abstract

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.