Conclusions
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1.
The alkylation of 2,2,6,6-tetramethyl-4-oxopiperidine enamines with Mannich bases gave 3-(2-acylethyl)-2,2,6,6-tetramethyl-4-oxopiperidines, which were converted to the corresponding nitroxyl radicals by oxidation with the H2O2-Na2WO4 system.
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2.
Analogous stable products can be obtained by the hydrolysis of the alkylation products of 2,2,6,6-tetramethyl-4-oxopiperidine-1-oxyl enamines with Mannich bases.
Literature cited
É. G. Rozantsev, Free Iminoxyl Radicals [in Russian], Khimiya (1970).
É. G. Rozantsev and V. D. Sholle, Usp. Khim.,40, 417 (1971).
A. G. Cook (editor), Enamines: Synthesis, Structure, and Reactions, New York-London (1969).
H. Hellman and G. Opitz,α-Aminoalkylierung, Weinheim (1960).
G. Opitz and H. Holtmann, Ann. Chem.,684, 79 (1965).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1639–1642, July, 1976.
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Mikhailov, V.I., Sholle, V.D., Kagan, E.S. et al. Reaction of Mannich bases with 2,2,6,6-tetramethylpiperidone enamines. Russ Chem Bull 25, 1555–1557 (1976). https://doi.org/10.1007/BF00920845
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DOI: https://doi.org/10.1007/BF00920845