Summary
-
1.
With geranic acid and its ester as examples, the applicability of low-temperature cyclization to isoprenoid acids was demonstrated.
-
2.
The effect of reaction conditions on the course of the cyclization of methyl geranate was studied, and suggestions were made concerning the identities of the intermediate products.
-
3.
α-Cyclogeranic acid and its ester can be converted only with difficulty into the corresponding β -isomers.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
V. A. Smit, A. V. Semenovskii, V. M. Medvedeva, and V. F. Kucherov, Dokl. AN SSSR124, 1080 (1959).
V. A. Smit, A. V. Semenovskii, and V. F. Kucherov, Izv. AN SSSR, Otd. khim, n.1960, 2193.
A. V. Semenovskii, V. A. Smit, and V. F. Kucherov, Dokl. AN SSSR132, 1107 (1960).
K. Bernhauer and R. Forster, J. Prakt. Chem.147, 199 (1936).
G. Stork and A. Burgstahler, J. Am. Chem. Soc.77, 5068 (1955).
P. Stadler, A. Eschenmoser, H. Schinz, and G. Stork, Helv. chim. acta40, 2191 (1957).
B. A. Rudenko, V. F. Kucherov, V. A. Smit, and A. V. Semenovskii, Izv. AN SSSR, Otd. khim. n.1962, 236.
F. Tiemann, Ber.33, 3710 (1900).
L. Purlee and R. Taft, J. Am. Chem. Soc.78, 5807 (1956).
Author information
Authors and Affiliations
Additional information
For previous communications see [1–3].
Rights and permissions
About this article
Cite this article
Smit, V.A., Semenovskii, A.V., Vlad, P.F. et al. Cyclization of isoprenoid compounds. Russ Chem Bull 11, 289–293 (1962). https://doi.org/10.1007/BF00908037
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00908037