Abstract
Dehydration of 2-hydroxy-8-R-tricyclo[7.3.1.02 , 7]tridecan-13-ones (R = H, Me, Ph) effected by various reagents provided 8-R-tricyclo[7.3.1.02 , 7]tridecen-13-ones with different positions of the double bond. In the presence of phosphoric acid arise isomers with the double bond in 2(3) position, a mixture of hydrochloric and acetic acid primarily affords isomers with the double bond in 2(7) position that further migrates into 7(8) position at R = Me, Ph.
Similar content being viewed by others
REFERENCES
Adesogan, E.K., J. Chem. Soc., C, 1968, no. 16, pp. 1974–1977; Fallis, A.G., Canad. J. Chem.-Rev. Canad. Chem., 1979, vol. 57, no. 23, pp. 3088–3089; Liu, H.J. and Dieckabularach, T., Heterocycles, 1987, vol. 25, no. 1, pp. 245–249; Sanni, S.B., Behm, H., and Beurskens, P.T., Acta Crystallogr., Sect. C, 1987, vol. 43, no. 7, pp. 1400–1403; Daniewski, W.M., Gumulka, M., Daniiewicz, W., Gluzinski, P., Krajewski, J., Pankowska, E., Bloszyk, E., Jacobsson, U., Norin, T., and Szafranski, F., Phytochemistry, 1993, vol. 33, no. 6, pp. 1534–1536; Inada, A., Konishi, M., Murata, H., and Nakanishi, T., J. Nat. Prod., 1994, vol. 57, no. 10, pp. 1446–1449; Govindachari, T.R., and Kumari, G.N.K., Phytochemistry, 1998, vol. 47, no. 7, pp. 1423–1425; Govindachari, T.R., Suresh, G., Banumathy, B., Masilamani, S., Gopalakrishnan, G., and Kumari, G.N.K., J. Chem. Ecol., 1999, vol. 25, no. 4, pp. 923–933.
Tilichenko, M.N., Nauchnyi Ezhegodnik Saratov. Univ., 1955, pp. 500–504; Plesek, J. and Munk, P., Coll. Czech. Chem. Commun., 1957, vol. 22, pp. 1596–1600; Julia, S. and Varech, D., Bull. Soc. Shim., 1959, no. 738, pp. 1127–1133.
Tilichenko, M.N., Uchenye Zapiski Saratov. Univ., 1959, vol. 71, pp. 153–158.
Barbulescu, N.S. and Leca, M., Rev. Roum. Shim., 1974, vol. 19, no. 8, pp. 1381–1391.
Pettit, G.R., Thomas, E.G., and Herald, G.L., J. Org. Chem., 1981, vol. 46, no. 21, pp. 4167–4171.
Cocker, W. and Shannon, P.V.R., J. Chem. Res. (Miniprint)., 1990, pp. 0801–0829.
Kriven'ko, A.P., Nikolaeva, T.G., Yudovich, L.M., Kolyagin, N.T., Yanovskii, A.I., Struchkov, Yu.T., and Kharchenko, V.G., Zh. Org. Khim., 1987, vol. 23, no. 5, pp. 1000–1008.
Lewis, J.W., Myers, P.L., and Readhead, M.J., J. Chem. Soc., C, 1970, no. 6, p. 771.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Rostovskaya, M.F., Vysotskaya, T.A., Grigorchuk, V.P. et al. Synthesis and Isomerization of Tricyclo[7.3.1.02,7]tridecen-13-ones. Russian Journal of Organic Chemistry 37, 1414–1417 (2001). https://doi.org/10.1023/A:1013423205456
Issue Date:
DOI: https://doi.org/10.1023/A:1013423205456