Abstract
Reactions of (-)-carvone with aliphatic, aromatic, heterocyclic, and functional thiols, catalyzed with potassium carbonate, gave the corresponding derivatives in high yields. Isopropyl mercaptan, 2-mercaptoethanol, furfuryl mercaptan, and N-acetylcysteine add across the endocyclic double bond of (-)-carvone with the predominant formation of the isomers with the S configuration of C3, whereas addition of hexadecyl mercaptan and 1,2-ethanedithiol mainly yields the R isomers.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Bachi, M.D., Bilokin, Y.V., and Melman, A., Tetrahedron Lett. 1998, vol. 39, no. 19, p. 3035.
Shing, T.K.M., Lo, H.Y., and Mak, T.C.W., Tetrahedron 1999, vol. 55, no. 28, p. 4643.
Carter, R., Hodgetts, K., McKenna, J., Magnus, P., and Wren, S., Tetrahedron 2000, vol. 56, no. 26, p. 4367.
Wattenberg, I.W., Sparnins, V.L., and Barany, G., Cancer Res. 1989, vol. 49, no. 10, p. 2689.
Hargreaves, M.K. and Rabari, L.F., Monatsh. Chem. 1983, vol. 114, no. 8, p. 195.
Morgunova, V.A., Nikitina, L.E., Plemenkov, V.V., Chugunov, Yu.V., and Fazlyeva, M.G., Zh. Org. Khim. 2000, vol. 36, no. 4, p. 512.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Ngo Bakopki, B., Palei, R.V. & Plemenkov, V.V. Synthesis of Sulfur-Containing Polyfunctional Terpenoids from (-)-Carvone. Russian Journal of General Chemistry 73, 630–633 (2003). https://doi.org/10.1023/A:1025613208685
Issue Date:
DOI: https://doi.org/10.1023/A:1025613208685