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Issue 10, 2011
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A persistent (amino)(ferrocenyl)carbene

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Abstract

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.

Graphical abstract: A persistent (amino)(ferrocenyl)carbene

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Supplementary files

Article information


Submitted
27 Feb 2011
Accepted
21 Mar 2011
First published
18 Apr 2011

New J. Chem., 2011,35, 2037-2042
Article type
Paper

A persistent (amino)(ferrocenyl)carbene

A. DeHope, D. Mendoza-Espinosa, B. Donnadieu and G. Bertrand, New J. Chem., 2011, 35, 2037
DOI: 10.1039/C1NJ20170K

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