Abstract
Ethyl α-halo-α-nitropropionate and -butyrate were prepared by alkylating ammonium salts of ethyl bromo- and chloronitroacetates. The addition of alkyl acrylates to alkyl chloronitroacetates or their salts gives dialkyl α-chloro-α-nitroglutarates. Sodium salts of ethyl α-nitro-α-sulfo-β-hydroxypropionate and -butyrate were obtained by the sulfodehalogenation of ethyl α-chloro-α-nitro-β-hydroxypropionate and -butyrate with sodium dithionite. Esters of α-amino acid hydrochlorides were prepared by the reduction of alkyl α-chloro-α-nitrocarboxylates. The hydrogenation of alkyl nitrosulfoacetates leads to the corresponding disodium salts of alkyl aminodisulfoacetates and piperazine-2,5-dione.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. I. Yurtanov, V. I. Anufriev, E. V. Kulish, N. G. Mikhailyuchenko, and I. I. Shulyak,Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 823 [Bull Acad. Sci. USSR, Div. Chem. Sci., 1991,40, 721 (Engl. Transl.)].
I. V. Martynov, Yu. L. Kruglyak. and S. P. Makarov,Zh. Obshch. Khim., 1963,33, 3382 [J. Gen. Chem. USSR, 1963,33 (Engl. Transl.)].
I. V. Martynov and Yu. L. Kruglyak, inProblemy organicheskogo sinteza [Problems of Organic Synthesis], Nauka, Moscow-Leningrad, 1965, 57 (in Russian).
A. I. Yurtanov and I. V. Martynov,Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 2729 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989,38, 2497 (Engl. Transl.)].
I. V. Martynov, V. O. Zavel'skii, S. V. Kovalenko, and A. I. Yurtanov,Izv. Akad. Nauk SSSR, Ser. Khim., 1982, 1029 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1982,31, No. 5 (Engl. Transl.)].
I. V. Martynov, V. O. Zavel'skii, S. V. Kovalenko, V. I. Fetisov, and A. I. Yurtanov,Dokl. Akad. Nauk SSSR, 1983,269, 152 [Dokl. Chem., 1983,269 (Engl. Transl.)].
I. V. Martynov and A. I. Yurtanov,Usp. Khim., 1989,58, 1474 [Russ. Chem. Rev., 1989,58 (Engl. Transl.)].
A. I. Yurtanov, E. S. Naidovskii, Yu. P. Belov, and I. V. Martynov,Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 1162 [Bull. Acad. Sci. USSR, Div. Chem. Sci, 1987,36, 1076 (Engl. Transl.)].
A. I. Yurtanov, A. N. Chekhlov, and I. V. Martynov,Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 1430 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987,36, 1323 (Engl. Transl.)].
A. I. Yurtanov, A. V. Yarkov, T. I. Ignat'eva, V. O. Zavel'skii, B. K. Beznosko, O. V. Novikova, V. N. Semenova, and I. V. Martynov,Izv. Akad. Nauk SSSR, Ser. Khim., 1988, 2549 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988,37, 2299 (Engl. Transl.)].
A. N. Chekhlov, A. I. Yurtanov, and I. V. Martynov,Dokl. Akad. Nauk SSSR, 1987,295, 618 [Dokl. Chem., 1987, 295 (Engl. Transl.)].
I. S. Ivanova-Karsakova, N. N. Bulatova, and S. S. Novikov,Izv. Akad. Nauk SSSR, Ser. Khim., 1962, 921 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1962, No. 5 (Engl. Transl.)].
I. V. Martynov, E. V. Stoyankova, and A. I. Yurtanov,Zh. Org. Khim., 1982,13, 1849 [J. Org. Chem. USSR, 1982,13 (Engl. Transl.)].
L. W. Kissinger and H. E. Ungnade,J. Org. Chem., 1958,23, 1517.
A. I. Yurtanov, V. I. Shestov, and I. V. Martynov,Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 2012 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990,39, 1826 (Engl. Transl.)].
A. I. Yurtanov, S. V. Kovalenko, and I. V. Martynov,Izv. Akad. Nauk SSSR, Ser. Khim., 1985, 2814 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985,34, 2610 (Engl. Transl.)].
Aldrich Library of NMR Spectra, 2th Ed., Aldrich Chem. Corp., New York,1, 666.
Dictionary of Organic Compounds, 5th Ed., Ch. Hall, New York, 1982,96, 2765, 5681.
A. K. Macbeth and D. Trail,J. Chem. Soc., 1925,127, 892.
J. P. Greenstein and M. Winitz,Chemistry of the Amino Acids, John Wiley & Sons, New York, 1961.
Author information
Authors and Affiliations
Additional information
For communication 5 seeIvz. Akad. Nauk SSSR, Ser. Khim., 1990, 2012 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990,39, 1826].
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 872–876, May, 1994.
Rights and permissions
About this article
Cite this article
Yurtanov, A.I., Baidildaeva, S.K., Chekhlov, A.N. et al. Substitution of halogen atom in α-halonitro compounds of the aliphatic series. Russ Chem Bull 43, 816–820 (1994). https://doi.org/10.1007/BF00717345
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00717345