Conclusions
-
1.
The oxidation the isomers of 7-acetoxy-Δ4-dodecahydro-4b-methyl-1,2-dicarboxylic acid and its diester with trans annellation of the A and B rings and a cis arrangement of the carboxyls and the angular methyl group with peroxyacetic acid goes stereospecifically and leads to epoxides in which the epoxide ring is trans relative to the carboxy groups. On the other hand, the analogous oxidation of the anhydride of the same steric series leads to the isomer with the cis arrangement of these groups.
-
2.
The configurations of the epoxides obtained were determined on the basis of some transformations of these compounds and an examination of molecular models.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
V. F. Kucherov, I. M. Mil'shtein, and I. A. Gurvich, Zh. obshch. khimii32, 765 (1962).
V. F. Kucherov, G. M. Segal', and I. N. Nazarov, Izv. AN SSSR. Otd. khim. n.1959, 673, 682; V. F. Kucherov, G. M. Segal', and I. N. Nazarov, Zh. obshch. khimii29, 804 (1959).
D. H. R. Barton and C. I. W. Brooks, J. Chem. Soc.1951, 257.
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 875–878, May, 1966.
Rights and permissions
About this article
Cite this article
Gurvich, I.A., Mil'shtein, I.M. & Kucherov, V.F. Stereochemistry of cyclic compounds Communication 65. Stereochemistry of the oxidation of one of the geometric isomers of 7-acetoxy-Δ4-dodecahydro-4b-methyl-1,2-phenanthrenedicarboxylic acid and its derivatives. Russ Chem Bull 15, 837–839 (1966). https://doi.org/10.1007/BF00849382
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00849382