Conclusions
-
1.
The formation of the anion-radicals (AR) of the corresponding nitroalkoxybenzenes is observed in the reactions of the o-, m-, and p-nitroanisoles and p-nitrophenetole with alkali metal alkoxides, the rate for the formation and destruction of which changes in the order: CH3ONa<C2H5ONa<t-C4H9OK.
-
2.
The rates for the formation of the AR of nitroalkoxybenzenes in the reactions with CH3ONa increase with increase in the concentration of the reagent and substrate and the amount of DMSO in its mixture with CH3OH. The substituents in the substrate lower the rate in the order: m-OCH3>p-OCH3>o-OCH3, which corresponds to the change in the acceptor capacity of the compounds.
Similar content being viewed by others
Literature cited
S. M. Shein, L. V. Bryukhovetskaya, N. M. Bazhin, V. N. Panfilov, and V. V. Voevodskii, Abstracts of Eighth International Symposium on Free Radicals [in Russian], Novosibirsk (1967), p. 167; S. M. Shein, L. V. Bryukhovetskaya, F. V. Pishchugin, V. F. Starichenko, V. N. Panfilov, and V. V. Voevodskii, Zh. Strukt. Khim.,11, 243 (1970); S. M. Shein, L. V. Bryukhovetskaya, A. D. Khmelinskaya, V. F. Starichenko, and T. M. Ivanova, Reaktsionnaya Sposobnost Organicheskikh Soedinenii, Tartuskii Gos. Univ., No. 4 (22), 1087 (1969).
L. A. Blyumenfel'd, L. V. Bryukhovetskaya, G. V. Fomin, and S. M. Shein, Zh. Fiz. Khim.,44, 931 (1970).
S. M. Shein, L. V. Bryukhovetskaya, and T. M. Ivanova, Izv. Akad. Nauk SSSR, Ser. Khim., 1594 (1973).
S. M. Shein and A. D. Khmelinskaya, Zh. Org. Khim.,4, 2160 (1968).
K. A. Bilevich and O. Yu. Okhlobystin, Usp. Khim.,37, 2162 (1968); S. P. Solodovnikov and A. I. Prokof'ev, ibid.,39, 1276 (1970).
C. A. Kingsbury, J. Org. Chem.,29, 3262 (1964).
N. M. Emanuel', E. T. Denisov, and Z. K. Maizus, Chain Reactions for Oxidation of Hydrocarbons in the Liquid Phase [in Russian], Nauka (1965), pp. 119, 122; E. A. Blyumberg and N. M. Emanuel', Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 274 (1957).
N. M. Emanuel', Dokl. Akad. Nauk SSSR,95, 603 (1954).
P. Ashmore, Catalysis and Inhibition of Chemical Reactions [Russian translation], Mir (1966), p. 361.
S. Benson, Principles of Chemical Kinetics [Russian translation], Mir (1964), p. 295; A. M. Goodale, Trans, Faraday Soc.,54, 195 (1958).
R. Foster and C. A. Fyfe, Rev. Pure Appl. Chem.,16, 61 (1966); N. J. Strauss, Chem. Rev.,70, 667 (1S)70).
J. B. Ainscough and E. F. Caldin, J. Chem. Soc., 2528 (1956).
V. F. Starichenko, V. P. Sokolov, and S. M. Shein, Izv. Akad. Nauk SSSR, Ser. Khim., 1839 (1971).
S. M. Shein, A. D. Khmelinskaya, and V. V. Brovko, Zh. Org. Khim.,6, 781 (1970).
C. Jackson and F. H. Gazzolo, J. Am. Chem. Soc.,23, 384 (1900); S. S. Gitis and A. I. Glaz, Zh. Obshch. Khim.,27, 1897 (1957).
S. S. Gitis, A. I. Glaz, and A. Ya. Kaminskii, Zh. Obshch. Khim.,33, 3301 (1963).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1601–1608, July, 1973.
Rights and permissions
About this article
Cite this article
Bryukhovetskaya, L.V., Mironova, L.V. & Shein, S.M. Anion-radicals in reactions of mono- and trinitroalkoxybenzenes with alkali metal alkoxides. Russ Chem Bull 22, 1550–1555 (1973). https://doi.org/10.1007/BF00930059
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00930059