Abstract
Compounds of general formulatrans-ArNi(PR3)2OAr' (R = Et, cyclohexyl; Ar = 2-MeC6H4, 2-FC6H4; Ar' = 4-FC6H4, 4-NO2C6H4) were synthesized by the reaction of Ar'OK with cationic nickel complexes generated by treatment of ArNi(PR3)2Cl with TlBF4. Syntheses of 4-fluorophenoxide complexes, ArNi(PR3)2OC6H4F-4, additionally give some quantities oftrans-[ArNi(PR3)2OC6H4F-4]⋯[HOC6H4F-4] adducts. Exchange reactions MeC6H4Ni(PEt3)2OC6H4F-4 + XC6H4OH ⇌ 2-MeC6H4Ni(PEt3)2OC6H4X + 4-FC6H4OH were studied in THF. The equilibrium is shifted to the right as the acidity of ArOH increases. A linear relationship between lgK eq and pK a of XC6H4OH in DMSO was found. A conclusion concerning the strong polarization of the Ni-O bond was made on the basis of an analysis of the chemical shifts of fluorine atoms in 2-MeC6H4Ni(PEt3)2OC6H4F-4.
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G. I. Drogunova, L. S. Isaeva, A. S. Peregudov, and D. N. Kravtsov.Metalloorg. Khim., 1991,4. 659 [Organomet. Chem. USSR, 1991,4, 328 (Engl. Transl.)].
A. S. Peregudov, G. I. Drogunova, L. S. Isaeva, E. I. Fedin, and D. N. Kravtsov,Metalloorg. Khim., 1991,4, 90 [Organomet. Chem. USSR, 1991,4, 47 (Engl. Transl.)].
L. M. Epshtein, L. N. Saitkulova, E. S. Shubina, L. S. Isaeva, G. I. Drogunova. and D. N. Kravtsov,Metalloorg. Khim., 1990,3, 305 [Organomet. Chem. USSR, 1990,3, 143 (Engl. Transl.)].
C. A. Tolman,J. Am. Chem. Soc., 1970,92, 923.
C. A. Tolman,Chem. Rev., 1977,77, 313.
R. G. Pearson,Inorg. Chem., 1988,27, 734.
H. F. Klein and H. H. Karsch,Chem. Ber. 1973,106, 1433.
T. Yamamoto, T. Kohara, and A. Yamamoto,Bull. Chem. Soc. Jpn., 1981,54, 2010.
M. Anton and J. M. Coronas,Inorg. Chim. Acta, 1979,36, 173.
J. M. Coronas,J. Organometal. Chem., 1976,121, 265.
K. Issleib and A. Brack,Z. Anorg. Allgem. Chem., 1954,277, 259.
Y. J. Kim, K. Osakada, A. Takenaka, and A. Yamamoto,J. Am. Chem. Soc., 1990,112, 1096.
K. Kalfus, J. Socha, and M. Vecera,Collect. Czech. Chem. Commun., 1974,39, 275.
F. G. Bordwell, R. J. McCallum, and W. N. Olmstead,J. Org. Chem., 1984,49, 1424.
R. W. Taft, E. Price, I. R. Fox, I. C. Lewis, K. K. Andersen, and G. T. Davis,J. Am. Chem. Soc., 1963,85, 3146.
A. N. Nesmeyanov, D. N. Kravtsov, B. A. Kvasov, E. M. Rokhlina, V. M. Pachevskaya, L. S. Golovchenko, and E. I. Fedin,J. Organometal. Chem., 1972,38, 307.
N. Kornblum and A. P. Lurie,J. Am. Chem. Soc., 1950,81, 2705.
M. Fujio, R. T. McIver, and R. W. Taft,J. Am. Chem. Soc., 1981,103, 4017.
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Translated fromIvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2266–2271, November, 1995.
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Peregudov, A.S., Drogunova, G.I. & Kravtsov, D.N. Aryl-bis(triorganylphosphine)nickel phenoxides. Russ Chem Bull 44, 2172–2178 (1995). https://doi.org/10.1007/BF00696726
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DOI: https://doi.org/10.1007/BF00696726