Abstract
2-Nitro-1,3-dicarbonyl and α-nitromonocarbonyl compounds were synthesized in the yields varying from moderate (30 %) to nearly quantitative by the nitration of β-dicarbonyl compounds in a two-phase system: sulfuric/nitric acid mixture-chloroform at - 10÷10 °C. The use of phase transfer conditions made it possible to avoid the formation of furoxans as by-products and to simplify the isolation of products. This method is quite common for preparing various α-functional nitro compounds including those containing a CF3-group. Key words: nitration, α-functional nitro compounds.
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References
M. T. Shipchandler,Synthesis, 1979, 666.
D. I. Weisblat and D. A. Lyttle,J. Am. Chem. Soc., 1949,71, 3079;
T. Shimizu, Y. Hayashi, and K. Teramura,Bull. Chem. Soc. Japan, 1985,58, 2519.
S. G. Zlotin, G. N. Varnaeva, and O. A. Luk'yanov,Usp. Khim., 1989,58, 796 [Russ. Chem. Revs., 1989,58 (Engl. Transl.)]
R. H. Fischer and H. M. Weitz,Synthesis, 1980, 261.
L. I. Khmel'nitskii, S. S. Novikov, and T. I. Godovikova,Khimiya furoksanov. Stmenie i sintez [Chemistry of Furoxans. Structure and Synthesis], Nauka, Moscow, 1981 (in Russian).
T. Simmons and K. Kreus,J. Org. Chem., 1968,33, 836.
K, K. Babievskii, E. I. Matrosov, and P. V. Petrovskii,Izv. Akad. Nauk SSSR, Ser. Khim., 1971, 2614 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1971,20, 2490 (Engl. Transl.)].
I. D. Lebedeva, I. L. Ryadnenko, and I. K. Kucherova,Zh. Fiz. Khim., 1968,42, 1827 [Russ. J. Phys. Chem., 1968,42 (Engl. Transl.)].
S. Sifniades,J. Org. Chem., 1975,40, 3562.
M. J. Thompson and P. J. Zeegers,Tetrahedron Lett., 1988,29, 2471.
D. S. Ross, K. F. Kuhlmann, and R. Malhotra,J. Am. Chem. Soc., 1983,105, 4299.
M. Sampoli, A. De Santis, and N. C. Marziano,J. Phys. Chem., 1985,89, 2864.
I. M. Medvetskaya, M. I. Vinnik, T. S. Kopytova, Yu. N. Matyushin, Yu. A. Lebedev, and V. F. Zhilin,Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 306 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990,39, 251 (Engl. Transl.)].
A. S. Morkovnik,Usp. Khim., 1988,57, 254 [Russ. Chem. Revs., 1988,57 (Engl. Transl.)].
A. L. Laikhter, T. I. Cherkasova, L. G. Mel'nikova, B. I. Ugrak, A. A. Fainzil'berg, and V. V. Semenov,Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1849 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 1637 (Engl. Transl.)].
V. Grakauskas and A. M. Guest,J. Org. Chem., 1978,43, 3485.
J. Lalonde, D. Bergbreiten, and C. H. Wong,J. Org. Chem., 1988,53, 2322.
V. P. Kukhar', Yu. L. Yagupol'skii, and V. A. Soloshonok,Usp. Khim., 1990,59, 149 [Russ. Chem. Revs., 1990,59 (Engl. Transl.)].
K. K. Babievskii, V. I. Bakhmutov, and V. M. Belikov,Izv. Akad. Nauk SSSR, Ser. Khim., 1978, 1293 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1978,27, 1125 (Engl. Transl.)].
E. I. Matrosov and K. K. Babievskii,Izv. Akad. Nauk SSSR, Ser. Khim., 1972, 2627 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1972,21, 2567 (Engl. Transl.)].
A. Brändström and U. Junggren,Acta Chem. Scand., 1969,23, 2204.
K. Ziegler, H. Erberle, and H. Ohlinger,Lieb. Ann. Chem., 1933,504, 94.
K. Uneyama and K. Ueda,Chem. Lett., 1988,5, 853.
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Translated fromIzvestiya Akademn Nauk. Seriya Khimicheskaya, No. 1, pp. 76–79, January, 1994.
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Kislyi, V.P., Laikhter, A.L., Ugrak, B.I. et al. Synthesis of α-functional nitro compounds by the nitration of activated carbonyl compounds in a two-phase system. Russ Chem Bull 43, 70–74 (1994). https://doi.org/10.1007/BF00699138
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DOI: https://doi.org/10.1007/BF00699138