Acetals of lactams and acid amides
- 28 Downloads
The reduction of 1-methyl-2-(2-benzoyl)methylenepyrrolidine, hexahydroazepines IIa–c, and (β-dimethylamino-β-methyl)methyleneacetophenone III in aprotic media on a dropping mercury electrode proceeds in two one-electron steps to give the corresponding enamines with a benzhydryl residue in the 2′ position. The regular dependence of the E1/2 values of the first waves in the reduction of enamino ketones IIa–c on the ring size is discussed: six-membered enamino ketone IIb is reduced most easily, while five-membered IIa is reduced with the greatest difficulty. It is shown that the ring size of the enamino compounds affects the E1/2 values only in those cases in which a change in the hybridization of the ring carbon atom occurs during electrical reduction.
KeywordsMercury Amide Carbon Atom Ketone Great Difficulty
Unable to display preview. Download preview PDF.
- 1.V. G. Granik, A. M. Zhidkova, R. G. Glushkov, A. B. Grigor'ev, M. K. Polievktov, T. F. Vlasova, and O. S. Anisimova, Khim. Geterotsikl. Soedin., No. 10, 1348 (1977).Google Scholar
- 2.A. B. Grigor'ev, V. G. Granik, and M. K. Polievktov, Zh. Obshch. Khim., 46, 404 (1976).Google Scholar
- 3.Ya. F. Freimanis, Ya. P. Stradyn', and I. Ya. Kravis, Zh. Obshch. Khim., 39, 631 (1969).Google Scholar
- 4.J. Zimmer, J. Richards, J. Turner, and D. Evans, Anal. Chem., 43, 1000 (1971).Google Scholar
- 5.R. Huisgen, H. Braude, H. Walz, and I. Glogger, Ber., 90, 1437 (1957).Google Scholar
- 6.Y. L. Gol'dfarb, and L. M. Belen'kii, Usp. Khim., 29, 470 (1970).Google Scholar
- 7.V. G. Granik, I. B. Marchenko, E. O. Sochneva, T. F. Vlasova, A. B. Grigor'ev, M. K. Polievktov, and R. G. Glushkov, Khim. Geterotsikl. Soedin., No. 11, 1505 (1976).Google Scholar
- 8.A. A. Vlced, Chem. Listy, 48, 1863 (1954).Google Scholar