Abstract
The sodium salt of [B12H12]2− dianion reacts with carboxylic acid halides to give a mixture of B-acylated product [B12H11COR]2− and an unstable intermediate, the latter undergoing hydrolysis to form [B12H11OH]2−. The ratio of the products formed depends on the nature of the radical R. The reaction mechanism was studied by NMR spectroscopy. A number of novel [B12H11COR]2− compounds were synthesized; their structures were confirmed by NMR and IR spectral data.
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K. M. Harmon, A. B. Harmon, and A. A. MacDonald,J. Am. Chem. Soc., 1969,91, 323.
R. V. Bismark and W. Preetz,J. Organomet. Chem., 1991,418, 147.
W. H. Knoth, I. C. Sauer, D. C. England, W. R. Hertles, and E. L. Muetterties,J. Am. Chem. Soc., 1964,86, 3973.
H. Hesse, H. Meir, and B. Zech,Spektroskopische Methoden in der organische Chemie, Georg Thieme Verlag, Stuttgart—New York, 1987.
H. O. Kalinowski, S. Berger, and S. Brown,13 C NMR Spectroscopie, Georg Thieme Verlag, Stuttgart—New York, 1984, 288.
M. F. Hawthorne, inChemistry of Boron and its Compounds, Ed. E. L. Muetterties, J. Wiley and Sons, Inc., New York, 1967, 226.
A. A. Semioshkin, P. V. Petrovskii, I. B. Sivaev, E. G. Balandina, and V. I. Bregadze,Izv. Akad. Nauk, Ser. Khim., 1996, 722 [Russ. Chem. Bull., 1996,45, 683 (Engl. Transl.)].
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 980–985, May, 1998.
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Semioshkin, A.A., Petrovskii, P.V., Gabel, D. et al. Acylation of [B12H12]2− dianion by carboxylic acid halides. Russ Chem Bull 47, 950–955 (1998). https://doi.org/10.1007/BF02498167
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DOI: https://doi.org/10.1007/BF02498167