Conclusions
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1.
Alkylnitrones, derivatives of sterically hindered 3-imidazoline-3-oxides, are metalated by treatment with phenyllithium in ether solution.
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2.
Reaction of the Li derivatives of nitrones with aldehydes and ketones makes it possible to obtain aldol condensation products; reaction with esters leads toβ-oxonitrones.
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3.
β-Oxonitrones resemble theβ-diketones in their properties.
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Literature cited
V. V. Martin and L. B. Volodarskii, Khim. Geterotsikl. Soedin.,1979, 103.
V. D. Sholle, L. A. Krinitskaya, and E. G. Rozantsev, Izv. Akad. Nauk SSSR, Ser. Khim.,1969, 149.
V. V. Martin, V. S. Kobrin, and L. B. Volodarskii, Izv. Sibirsk. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk,1977, No. 7, Issue 3, 153.
J. Hamer and A. Macaluso, Chem. Rev.,64, 437 (1964).
L. B. Volodarskii, I. A. Grigor'ev, and G. A. Kutikova, Zh. Org. Khim.,9, 1974 (1973).
R. Bonnett, R. F. C. Brown, V. M. Clark, J. O. Sutherland, and A. Todd, J. Chem. Soc.,1959, 2094.
P. Beak and D. B. Reitz, Chem. Revs.,78, 275 (1978).
D. St. C. Black, V. M. Clark, B. G. Odell, and Lord Todd, J. Chem. Soc. Perkin Trans, 1,1976, 1944.
F. De Sarlo and G. Renzi, J. Chem. Soc. Perkin Trans, 1,1978, 1113.
E. W. Garbisch, J. Am. Chem. Soc.,85, 1696 (1963).
L. B. Volodarskii, V. A. Reznikov, and V. S. Kobrin, Zh. Org. Khim.,15, 415 (1979).
A. L. Buchachenko and A. M. Vasserman, Stable Radicals [in Russian], Khimiya (1973), p. 223.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1336–1344, June, 1980.
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Martin, V.V., Volodarskii, L.B. Tautomerism and chemical properties of β-oxonitrones. Russ Chem Bull 29, 956–962 (1980). https://doi.org/10.1007/BF00958816
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DOI: https://doi.org/10.1007/BF00958816