Conclusions
-
1.
The pure trans-isomers of the 1-bromomethyl-, 1-iodomethyl- and 1-chloromethyl-4, 6-dimethyl-3-cyclohexenes were synthesized.
-
2.
A study was made of the epimerization of the 1-halomethyl- and 1-hydroxymethyl-4, 6-dimethyl-3-cyclohexenes under the influence of temperature and acid catalysts.
Similar content being viewed by others
Literature cited
G. P. Kugatova-Shemyakina, L. I. Rozhkova, V. N. Gramenitskaya, and V. M. Andreev, Zh. Organ. Khim.,7, 80 (1971).
G. P. Kugatova-Shemyakina, L. I. Rozhkova, V. N. Gramenitskaya, and V. M. Andreev, Zh. Organ. Khim.,6, 2446 (1970).
E. J. Corey and E. K. W. Wat, J. Am. Chem. Soc.,89, 2757 (1967).
J. M. Osborn, J. Chem. Soc., 5270 (1961).
J. Klein, Israel J. Chem.,1, 385 (1963).
E. Casadevall, C. Largeau, and P. Moreau, Bull. Soc. Chim. France, 1514 (1968).
T. I. Temnikova, Course on the Principles of Organic Chemistry [in Russian], Khimiya, Leningrad (1968).
D. G. Coe, S. P. Landauer, and H. M. Rydon, J. Chem. Soc., 2281 (1954).
M. Hanack and J. Höffner, Chem. Ber.,99, 1077 (1966).
E. N. Marvel, D. Sturmer, and R. S. Knutson, J. Org. Chem.,33, 2991 (1968).
J. Hooz and S. S. Gilani, Can. J. Chem.,46, 86 (1968).
J. E. Johnson, R. H. Blizzard, and H. W. Carhart, J. Am. Chem. Soc.,70, 3664 (1948).
H. Walborsky, L. Barash, and T. C. Davis, Tetrahedron,19, 2333 (1963).
C. K. Ingold, Structure and Mechanism in Organic Chemistry [Russian translation], IL (1959).
Author information
Authors and Affiliations
Additional information
Deceased.
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1102–1107, May, 1972.
The NMR spectra were taken by V. I. Sheichenko and were interpreted by T. M. Ivanova, to whom we express our sincere gratitude.
Rights and permissions
About this article
Cite this article
Kugatova-Shemyakina, G.P., Andreev, V.M. & Rozhkova, L.I. Stereochemistry and reactivity of unsaturated compounds. Russ Chem Bull 21, 1056–1060 (1972). https://doi.org/10.1007/BF00853768
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00853768