Insertion of phenyl isocyanide into ethanol catalysed simultaneously by copper(I) and base
- 1 January 1974
- journal article
- abstracts
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 93 (12) , 314-316
- https://doi.org/10.1002/recl.19740931204
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.Keywords
This publication has 13 references indexed in Scilit:
- Gold carbene complexes: preparation, oxidation, and ligand displacementJournal of Organometallic Chemistry, 1974
- The electronic structure of isocyanide ligands and the spectroscopic behaviour of MnII octahedral complexesJournal of Organometallic Chemistry, 1974
- An improved procedure for the Hofmann carbylamine synthesis of isonitrilesTetrahedron Letters, 1972
- Kinetics of nucleophilic attacks on palladium(II) isocyanide complexesInorganic Chemistry, 1972
- New isocyanide-platinum complexesJournal of the American Chemical Society, 1971
- Neues Verfahren zur Darstellung von IsocyanidenAngewandte Chemie, 1971
- A Gold(I) Carbene ComplexSynthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 1971
- Synthetic reactions by complex catalysts. XII. Copper-catalyzed reaction of isocyanide with alcoholCanadian Journal of Chemistry, 1969
- The equilibrium between ethoxide and hydroxide ions in ethanol and in ethanol–water mixturesJournal of the Chemical Society, 1954
- Properties of Electrolytic Solutions. II. The Evaluations of Λ0 and of K for Incompletely Dissociated ElectrolytesJournal of the American Chemical Society, 1933