D. Knol, C. P. A. van Os, W. Drenth
Apr 8, 1975
Citations
0
Influential Citations
8
Citations
Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
The insertion of phenyl isocyanide into ethanol under the influence of base and Cu(PhNC)4BF4 is investigated mechanistically. In pre-equilibria the BF4⊖ anion is exchanged for ⊖OC2H5. By intramolecular nucleophilic attack of ⊖OC2H5 on coordinated isocyanide an [(ethoxy)-(phenylimino)methyl]copper intermediate is formed. The substituent effect supports this conclusion. In a rapid reaction with ethanol the intermediate decomposes and the insertion product, ethyl N-phenylformimidate, is formed. It reacts slowly to give N,N′-diphenylformamidine, which is precipitated at the end of the reaction as a copper complex.