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Issue 12, 2006
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A new and convenient approach towards bis(iminophosphoranyl)methane ligands and their dicationic, cationic, anionic and dianionic derivatives

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Abstract

The availability of bis(aminophosphoranes) 2ac through a straightforward synthesis yielded access to a whole family of N,N ligands via sequential deprotonation. The obtained cationic 3ac, neutral 4ac, anionic 5ac and dianionic 6ac compounds were fully characterized by NMR and X-ray crystallography. Monocations 3ac were shown to result from the deprotonation of 2ac at the bridging methylene carbon. DFT calculations evidenced a substantial negative charge at this carbon. For the neutral bis(iminophosphoranes) 4ac, two different forms were experimentally observed depending on the nature of the substituent at nitrogen. In the presence of an aryl group, a bis(iminophosphorane) is obtained whereas with alkyl substituent a tautomeric form resulting from a (1,3) hydrogen shift is observed. Theoretical studies were in good agreement with experimental results showing that these two forms are close in energy. The structure obtained for monoanion 5a reveals that a substantial interaction occurs between the anionic carbon and the lithium cation. The X-ray crystal structure of the optically pure dianion 6b has also been recorded.

Graphical abstract: A new and convenient approach towards bis(iminophosphoranyl)methane ligands and their dicationic, cationic, anionic and dianionic derivatives

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Publication details

The article was received on 13 Jul 2006, accepted on 30 Aug 2006 and first published on 22 Sep 2006


Article type: Paper
DOI: 10.1039/B610049J
Citation: New J. Chem., 2006,30, 1745-1754
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    A new and convenient approach towards bis(iminophosphoranyl)methane ligands and their dicationic, cationic, anionic and dianionic derivatives

    M. Demange, L. Boubekeur, A. Auffrant, N. Mézailles, L. Ricard, X. Le Goff and P. Le Floch, New J. Chem., 2006, 30, 1745
    DOI: 10.1039/B610049J

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