Producción Científica Profesorado

A Persistent(Amino)(Ferrocenyl)carbene.

Mendoza Espinosa, Daniel


deHope, A.; Mendoza-Espinosa, D.; Donnadieu, B.; Bertrand, G. A Persistent(Amino)(Ferrocenyl)carbene. New J. Chem. 2011, 35, 2037-2042


Deprotonation of N,N-diisopropyl-C-ferrocenylaldiminium triflate 2 cleanly leads to the corresponding 1,2-diamino-1,2-diferrocenylethene 3, the dimer of the desired (amino)(ferrocenyl)carbene. Fulvene 6, obtained by addition of the lithium salt of tetramethylcyclopentadiene to methoxyformamidinium methylsulfate 5, reacts with dicarbonylcyclopentadienylbromoiron(II), and with a mixture of FeCl2 and Cp* lithium salt, affording the corresponding tetramethylferrocenylaldiminium salt 7, and nonamethylferrocenylaldiminium salt 8, respectively. Although the deprotonation of 7 gives a complex mixture of products, the treatment of 8 at ?78 C with sodium hexamethyldisilazide allowed for the isolation of the corresponding (amino)(ferrocenyl)carbene 9 as a yellow powder. However, even in the solid state, it is stable for less than 48 h at ?20 C. In addition to NMR spectroscopy, evidence for the carbene nature of 9 was found by a trapping experiment with sulfur that leads to the corresponding adduct 10, which was characterized by a single crystal X-ray diffraction study.

Producto de Investigación

Artículos relacionados

First Total Synthesis of ()-Flustraminol B

The absoluteconfiguration of cuauhtemone and related compounds

Aromatic Bromination versus Oxidation of Indolylmalonates by Bromine

Absolute configuration determination of 2-(2-oxo-3-indolyl)acetamide derivatives

Synthesis of ?4:?2-Exocyclic-Diene Iridium(I) Complexes Derived from 1,3-Oxazolidin-2-ones and Their...

Synthesis of Acetamido(indol-3-yl)propanol Derivatives

Transesterifications mediated by t-BuNH2

Conformational studies on indole alkaloids from Flustra foliacea by NMR and molecular modeling

Reactivity of TpMe2Ir(C2H4)(DMAD) with carboxylic acids. A DFT study on geometrical isomers and stru...

Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2