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Extra resources for Comprehensive Organometallic Chemistry 3ed Vol 08 Grp 10
It is interesting to mention that this compound is also formed when [Ni(C6F5)]42À is reacted with HCl in the presence of CO, indicating the preference of the electron-rich Ni center to bind CO over ClÀ. The hydroxide 24, prepared from the acetonitrile adduct 19, is a versatile starting material for the synthesis of a wide range of derivatives containing the Ni(C6F5)2 unit. This compound reacts with weak acids such as ArOH,35 RSH,36 C6F5NH2,37 or heterocycles,35,37 giving rise to the corresponding ArO, RS, C6F5NH, and heterocycle-bridged binuclear compounds.
Probably because of their ready availability, organomagnesium reagents are the most commonly used by far. In addition, they often allow the introduction of one organic group in a selective manner. Recent examples of selective monoalkylation reactions are shown in Equation (17)44 and Scheme 4. 45 Addition of PMe3 regenerates the cis-mononuclear derivative 38. ð17Þ Scheme 4 Nickel–Carbon -Bonded Complexes Table 4 Complexes of composition NiR2Ln R L Characterization Me Me Me Me Me Me Me (py)2 bipy Xyl-2,6-NTC(H)C(H)TNXyl-2,6 Xyl-2,6-NTC(Me)C(Me)TNXyl-2,6 DiPP-2,6-NTC(H)C(H)TNDiPP-2,6 DiPP-2,6-NTC(Me)C(Me)TNDiPP-2,6 BIAN(Ar)2, Ar ¼ Xyl, DiPP 1 Me, 45 Me Me Me (:CN(But)CHCHN)CH2CH2(NCHCH(But)NC:) dippe dippp dtbpe Me CD3 Et Prn, 74 Bui CH2CMe2Ph C(CN)3 C(CN)3 Bz Bz Bz CH2C6H4Me-2 CH2C6H4Me-2 CH2C6H4Me-2 CH2CN, 39 CH2SMe, 40 CH2SBut, 40 CH2SPh, 40 CH2TMS CH2TMS CH2TMS CH2TMS CH2TMS CH2SiMe2Ph CH2SiMe2Ph CH2SiMe2Ph cis-Mes trans-Mes Mes (C6H4OMe-2)2PCH2CH2P(C6H4OMe-2)2 dtbpe BIAN(Ar2), Ar ¼ Xyl, DiPPi BIAN(Ar2), Ar ¼ Xyl, DiPPi bipy (py)2 (2-Methylimidazole)2 (4-Methylimidazole)2 (py)2 bipy tmda dmpe depe dippe dppe (PBu3)2 (PBu3)2 (PBu3)2 (py)2 Xyl-2,6-NTC(H)C(H)TNXyl-2,6 Xyl-2,6-NTC(Me)C(Me)TNXyl-2,6 DiPP-2,6-NTC(H)C(H)TNDiPP-2,6 DiPP-2,6-NTC(Me)C(Me)TNDiPP-2,6 dmpe depe dippe (py)2 (py)2 bipy Mes 2,29-bispyrazine Mes 3,39,4,49-Me4Phen 3-pyrazolyl-1-Me-4CO2Me-5-Cl, 55 3-pyrazolyl-1,4-Me2-5Cl, 56 C6F5 C6F5 bipy C6F5, 47 CUC-Fc CUC-PBu3þ SbF6À bipy bipy R1NTC(R2)C(R2)TNR1R1 ¼ H, R2 ¼ Ph, o-Tol, p-Tol R1 ¼ Me, R2 ¼ Ph, o-Tol, p-Tol Ph2PCH2COPh (PBu3)2 (PBu3)2 13 H, C XR, EXAFS A, 1H, 13C A, 1H, 13C A, 1H, 13C A, 1H, 13C 1 H, 13C, dec > À10 C A, 1H, 13C, XR A, 1H, 13C, 31P A, 1H, 13C, 31P A, m/d, IR, 1H, 13C, 31 P, XR 1 H, 13C, 31P IR, 1H, 31P 1 H, 13C 1 H, 13C A, IR, 1H, 13C 1 H, 13C A, UV–VIS, IR A, UV–VIS, IR 1 H, 13C, XR 1 H, 13C 1 H, 13C A, 1H, 13C, 31P A, 1H, 13C, 31P A, 1H, 13C, 31P 1 H, 31P, dec > À40 C A, 31P, 13C, XR A, 31P, 13C, XR A, 31P, 13C, XR A, 1H, 13C A, 1H, 13C A, 1H, 13C A, 1H, 13C A, 1H, 13C A, 1H, 13C, 31P A, 1H, 13C, 31P A, 1H, 13C, 31P, XR A, 1H, 13C, XR 1 H, 13C A, UV–VIS, 1H, 13C, XR, EXAFS, CV A, UV–VIS, 1H, 13C, EXAFS A, UV–VIS, 1H, 13C, EXAFS A, 1H, m/d, UV–VIS, IR, XR A, 1H, m/d, UV–VIS, IR, XR A, 1H, 19F, XR A, IR, 1H, 19F XR, 1H, 13C, MS A, UV–VIS, IR, 1H, 13C A, IR, 31P, XR References 46 49,118 46,57 46 46,57 46 58 64 62 62 50 127 50 59 59 128 46 150 150 46 46 46 61 61 61 47 27 27 27 46 46 46 46,60 46,60 61 61 61 46 46 48,49,99 49 49 84,85 84,85 86,90 63 65 121 89 BIAN, ¼ bis(imino)acenaphtene; DiPP, 2,6-diisopropylphenyl; Xyl, 2,6-dimetylphenyl; A, elemental analysis; m/d: melting or decomposition point; Ãm: molar conductivity; MS, mass spectrum; UV, ultraviolet–visible; IR, infrared; 1H, 13C, 31P, 19F, 7Li, NMR spectra; XR: X-ray diffraction; CV, cyclic voltammetry; dec, decomposition temperature.
Although this compound decomposes by reductive elimination above À10 C, it has been structurally characterized. Carbon monoxide cleaves the halide dimers 20 (X ¼ Cl, Br, I) to the corresponding mononuclear carbonyls 22, but due to the presence of the potentially bridging halide ligands, the process is easily reversed. Replacement of the halide ligand by a third C6F5 group gives the more stable complex 23. It is interesting to mention that this compound is also formed when [Ni(C6F5)]42À is reacted with HCl in the presence of CO, indicating the preference of the electron-rich Ni center to bind CO over ClÀ.