Reaction of electrogenerated cyanomethyl anion with cyclohexylisocyanate: synthesis of N-(cyclohexylcarbamoyl)acetamide. An unexpected product was written by Scarano, Vincenzo;Bortolami, Martina;Pandolfi, Fabiana;Petrucci, Rita;Rocco, Daniele;Zollo, Giuseppe;Feroci, Marta. And the article was included in Journal of the Electrochemical Society in 2020.Reference of 2387-23-7 This article mentions the following:
The contamination with H2O of the cathodic ACN-Et4NBF4 solution gave the authors the opportunity to study alkyl isocyanate reactivity toward electrogenerated anions. The cathodic reduction of a ACN-Et4NBF4 solution gave both hydroxide and cyanomethyl anions. The reaction of the catholyte with cyclohexylisocyanate led to the exclusive formation of acetamidated product, with no traces of cyanomethylated one. On the contrary, when reacting with benzaldehyde only the cyanomethylated was isolated. Considering that the acetamidated product of benzaldehyde is reported to be unstable (thus its formation cannot be excluded), various experiments were carried out to understand the anomalous reactivity of cyclohexylisocyanate. Also, computational anal. allowed to state the higher stability of acetamidated product with respect to the cyanomethylated one. The possibility of a concerted reaction, instead of acetamide anion formation prior to the reaction, is still an open question. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Reference of 2387-23-7).
1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Reference of 2387-23-7
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics