Synthesis of 1,2-cyclopentadienyl diimine anions and ...

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Title Synthesis of 1,2-cyclopentadienyl diimine anions and their zirconium complexes
Author(s) Nola Etkin, C. M. Ong, D. W. Stephan
Journal Organometallics
Date 1998
Volume 17
Issue 17
Start page 3656
End page 3660
Abstract Abstract: 1,2-disubstituted cyclopentadienyl diimine anions are examples of extended -systems that bind metals through the nitrogen atoms. Reaction of Cp2Mg with benzonitrile gives the product (1,2-C5H3(C(Ph)NH)2)CpMg(NCPh) (1) in 98% yield. In an analogous manner, the related complexes (1,2-C5H3(C(Ph)NH)2)CpMg(OEt2) (2) and ((4-Me3SiC5H2)(1,2-(C(Ph)NH)2)(Me3SiC5H4)Mg(OEt2) (3) were prepared in situ. Demetalation of these complexes 1-3 yields the corresponding free diimine ligands of formulation H[(1,2-C5H3(C(Ph)NH)2)] (4) and H[4-Me3SiC5H2-1,2-(C(Ph)NH)2] (5). Hydrolysis of compound 4 leads to the fulvene derivative 1-(C(OH)Ph)-2-(O=C(Ph))C5H3 (6). The zirconium complexes (C5H3-1,2-(C(Ph)NH)2)ZrCl3(THF) (7) and (C5H3-1,2-(C(Ph)NH)2)3ZrCl (8) were isolated from reactions of 4 with ZrCl4(THF)2. X-ray crystallographic studies of 1, 7, and 8 are reported. Evidence suggests that these new 1,2-disubstituted cyclopentadienyl diimine anions impart some charge delocalization, thus offering a new approach to electrophilic metal centers. This view is supported by EHMO calculations.
DOI 10.1021/om980409l

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