Acylierung von Heterocyclen mit Kohlensäurederivaten. I. Kinetik und Mechanismus der Reaktion von 2‐Aminobenzimidazolen mit Arylcyanaten

• Published in: Journal für Praktische Chemie
• Main Authors: Bacaloglu, Ilse, The Ky, Truong, Boeriu, Carmen, Glatt, Hans Horst, Bacaloglu, Radu, Martin, Dieter, Graubaum, Heinz
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 1982
• Subjects: Carbonic acid
• Online Access: http://dx.doi.org/10.1002/prac.19823240514; http://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fprac.19823240514; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fprac.19823240514; https://onlinelibrary.wiley.com/doi/pdf/10.1002/prac.19823240514

Acylation of Heterocycles with Carbonic Acid Derivatives. I. Kinetics and Mechanism of the Reaction of 2‐Aminobenzimidazoles with Aryl Cyanates The second order rate constants for the reaction of 2‐amino‐benzimidazoles (2‐ABI) with aryl cyanates forming 2‐amino‐benzimidazole aryl ester imide 3 have been determined in dependence on substituent effects by u. v. measurements. The results are interpreted by a six‐membered cyclic transition state in which the electrophilic attack of the cyanate on the endocyclic N atom is catalyzed by an H bridge interaction of the exocyclic amino group of 2‐ABI with the OCN group.