Conclusions
-
1.
The formation of cycloalkoxy, α-hydroxycycloalkyl, and ω-formylalkyl radicals in the oxidation of secondary cycloalkanols by Pb(OAc)4 was recorded by an EPR method in the presence of spin traps.
-
2.
In the presence of the Pb(OAc)4-Cu(II) system, the ability of secondary cyclic alcohols to undergo oxidative decyclization with the formation of ω-alkenals decreases in the series cyclopentanol > cycloheptanol > cyclohexanol > cyclooctanol.
Similar content being viewed by others
Literature cited
N. I. Kapustina, S. S. Spektor, and G. I. Nikishin, Izv. Akad. Nauk. SSSR, Ser. Khim., 1541 (1983).
G. I. Nikishin, N. I. Kapustina, S. S. Spektor, and E. P. Kaplan, Izv. Akad. Nauk SSSR, Ser Khim., 1548 (1979).
N. I. Kapustina, S. S. Spektor, and G. I. Nikishin, Izv. Akad. Nauk SSSR, Ser. Khim., 2721 (1984).
M. Lj. Mihailovic, Ž. Cekovic, V. Andrejević, et al., Tetrahedron,24, 4947 (1968).
A. C. Cope, M. Gordon, S. Moon, and Chung Ho Park, J. Am. Chem. Soc.,87, 3119 (1965).
G. I. Nikishin and N. I. Kapustina, Izv. Akad. Nauk SSSR, Ser. Khim., 1345 (1984).
A. R. Forrester and S. P. Hepburn, J. Chem. Soc. C,4, 701 (1971).
E. G. Janzen and B. J. Blackburn, J. Am. Chem. Soc.,91, 4481 (1969).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2327–2331, October, 1988.
Rights and permissions
About this article
Cite this article
Kapustina, N.I., Popkov, A.Y., Gasanov, R.G. et al. Oxidation of secondary cyclic alcohols by Pb(OAc)4 catalyzed by Cu(II) compounds. Russ Chem Bull 37, 2095–2099 (1988). https://doi.org/10.1007/BF00953412
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00953412