Abstract
Triphenylbismuth diacylates, Ph3Bi(O2CR)2 (R = Me, Et, Ph, CF3, CH=CH2), are novel effective reagents for fine organic synthesis. They oxidize primary and secondary alcohols and di-tert-glycols under mild conditions to form the corresponding carbonyl compounds in high yields;O- andN-phenylate alcohols, enols, and amines; andO- ando-C-phenylate phenols.
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References
R. A. Abramovitch, D. H. R. Barton, and J. P. Finet,Tetrahedron, 1988,44, 3039.
T. I. Zinov'eva, T. G. Brilkina, and V. A. Dodonov,Tez. dokl. VIII Vsesoyuz. konf. po peroksidam [VIII-th All-Union Conference on Peroxides, Abstrs.], Leningrad, 1985, 72 (in Russian).
V. A. Dodonov, A. V. Gushchin, and T. G. Brilkina,Zh. Obshch. Khim, 1985,55, 73 [J. Gen. Chem. USSR, 1985,55 (Engl. Transl.)].
A. V. Gushchin, Ph. D. Thesis, Gor'kii State University, Gor'kii, 1986 (in Russian).
D. H. R. Barton, D. J. Lester, W. B. Motherwell, and M. T. B. Papoula,J. Chem. Soc., Chem. Commun., 1979, 705.
V. A. Dodonov, T. G. Brilkina, and A. V. Gushchin,Zh. Obshch. Khim., 1981,51, 2380 [J. Gen. Chem. USSR, 1981,51 (Engl. Transl.)].
V. A. Dodonov, T. G. Brilkina, and A. V. Gushchin,Zh. Obshch. Khim., 1984,54, 2157 [J. Gen. Chem. USSR, 1984.54 (Engl. Transl.)].
V. A. Dodonov, A. V. Gushchin, and T. G. Brilkina,Zh. Obshch. Khim, 1985,55, 2514 [J. Gen. Chem. USSR, 1985.55 (Engl. Transl.)].
D. H. R. Barton, J. P. Finet, and C. Pichon,J. Chem. Soc., Chem. Commun., 1986, 65.
S. David and A. Thieffry,Tetrahedron Lett., 1981,22, 5063.
H. Brunner, U. Obermann, and P. Wimmer,J. Organomet. Chem., 1986,316, C1.
D. H. R. Barton, J. C. Blazejewski, B. Charpiot, D. J. Lester, W. B. Motherwell, and M. T. B. Papoula,J. Chem. Soc., Chem. Commun., 1980, 287.
D. H. R. Barton, J. P. Finet, J. Khamsi, and C. Pichon,Tetrahedron Lett., 1986,27, 3619.
V. A. Dodonov, A. V. Gushchin, and T. G. Brilkina,Zh. Obshch. Khim., 1985,55, 466 [J. Gen. Chem. USSR, 1985,55 (Engl. Transl.)].
D. H. R. Barton, J. P. Finet, and J. Khamsi,Tetrahedron Lett., 1986,27, 3615.
D. H. R. Barton, J. P. Finet, and J. Khamsi,Tetrahedron Lett., 1989,30, 937.
V. A. Dodonov, A. V. Gushchin, D. F. Grishin, and T. G. Brilkina,Zh. Obshch. Khim., 1984,54, 100 [J. Gen. Chem. USSR, 1984,54 (Engl. Transl.)].
V. A. Dodonov and A. V. Gushchin,Metalloorg. Khim., 1990,3, 112 [J. Organomet. Chem. USSR, 1990,3 (Engl. Transl.)].
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2043–2047, December, 1993.
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Dodonov, V.A., Gushchin, A.V. Triphenylbismuth diacylates as novel reagents for fine organic synthesis. Russ Chem Bull 42, 1955–1959 (1993). https://doi.org/10.1007/BF00698873
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DOI: https://doi.org/10.1007/BF00698873