1-Alkyl-14-methyl-4-oxopiperidinium salts can be dealkylated quantitatively by means of lithium in liquid ammonia with preservation of the piperidine ring and the ketone function.
The course of the dealkylation depends neither on the position of the substituents in the ring, nor on their configuration.
The breaking of the N+-C bond depends on the nature of the alkyl substituent.
A method is proposed for the synthesis of 1-alkyl-4-piperidones from 1-methyl-4-piperidones which may find application for the structural correlation of 4-piperidones.
This is a preview of subscription content, log in to check access.
Buy single article
Instant access to the full article PDF.
Price includes VAT for USA
Subscribe to journal
Immediate online access to all issues from 2019. Subscription will auto renew annually.
This is the net price. Taxes to be calculated in checkout.
G. T. Katvalyan and É. L. Mistryukov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11 (1968).
É, L. Mistryukov and N. I. Aronova, Izv. Akad. Nauk SSSR, Ser. Khim., 783 (1967); 789 (1967).
E. Grovenstein and R. W. Stevenson, J. Am. Chem. Soc.,81, 4850 (1959).
D. Caine and B. J. L. Huff, Tetrahedron Letters, 4695 (1966).
W. L. Meyer and N. Sapianchay, J. Am. Chem. Soc.,86, 3343 (1964); R. Boghar and S. Szabo, Tetrahedron Letters, 2867 (1964); C. H. MacGillavry and G. Fodor, J. Chem. Soc., 597 (1964); H. O. House and C. G. Pitt, J. Org. Chem.,31, 1062 (1966); J. McKenna, J. M. Mckenna, A. Tulley, and J. White, J. Chem. Soc., 1711 (1965); 5439 (1965); C. D. Johnson, R. A. Y. Jones, A. R. Katritzky, C. R. Palmer, K. Schofield, and R. J. Wells, J. Chem. Soc., 6797 (1965); H. O. House, B. A. Tefertiller, and C. G. Pitt, J. Org. Chem.,31, 1073 (1966).
D. R. Howton, J. Org. Chem.,10, 277 (1945).
O. I. Sorokin, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 460 (1961).
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2023–2027, September, 1969.
About this article
Cite this article
Katvalyan, G.T., Mistryukov, É.A. Stereochemistry of the dequaternization of 1,1-dialkyl-4-oxopiperidinium salts. Russ Chem Bull 18, 1868–1872 (1969). https://doi.org/10.1007/BF00905826
- Structural Correlation