Abstract
Epoxidation, bromination, and iodination of the double bond in (+)-δ-cadinol under various conditions are accompanied by formation of 1,4- or 1,5-epoxy derivatives. By contrast, vicinal hydroxylation gives rise to “normal” products. Intramolecular cyclization of the resulting vicinal diols was studied.
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REFERENCES
Westfelt, L. Acta Chem. Scand., 1966, vol. 37, p. 2893.
Pentegova, V.A., Motl, O., and Herout, V., Collect. Czech. Chem. Commun., 1961, vol. 26, p. 1362.
Pentegova, V.A., Motl, O., and Herout, V., Dokl. Akad. Nauk SSSR, 1961, vol. 138, p. 850.
Aueg, W.A. and Browne, L.M., Tetrahedron, 1981, vol. 37, p. 2199.
Pentegova, V.A. and Dubovenko, Zh.V., Izv. Sib. Otd. Akad. Nauk SSSR, 1968, vol. 12, p. 110.
Motl, O., Sykora, V., Herout, V., and Sorm, F., Collect. Czech. Chem. Commun., 1958, vol. 23, p. 1297.
Rezvukhin, A.I., Babkin, V.A., and Dubovenko, Zh.V., Zh. Org. Khim., 1972, vol. 11, p. 2232.
Rezvukhin, A.I., Khan, V.A., and Dubovenko, Zh.V., Izv. Akad. Nauk SSSR, Ser. Khim., 1975, p. 1310.
Gatilov, Yu.V., Dubovenko, Zh.V., and Khan, V.A., Zh. Strukt. Khim., 1979, vol. 20, p. 509.
Gatilov, Yu.V. and Dubovenko, Zh.V., Khim. Prirodn. Soedin., 1979, p. 234.
Tkachev, A.V. and Denisov, A.Yu., Khim. Prirodn. Soedin., 1990, p. 635.
Tsypysheva, I.P., Kunakova, A.M., Spirikhin, L.V., Valeev, F.A., and Tolstikov, G.A., Russ. J. Org. Chem., 2001, vol. 37, p. 1666.
Valeev, F.A., Tsypysheva, I.P., Kunakova, A.M., and Tolstikov, G.A., Dokl. Ross. Akad. Nauk, 2002, vol. 382, p. 781.
Haines, A. H., Methods for the Oxidation of Organic Compounds. Akanes, Alkenes, Alkynes, and Arenes, London: Academic, 1985. Translated under the title Metody okisleniya organicheskikh soedinenii, Moscow: Mir, 1988, p. 399.
Selective Organic Transformation, Thyagarajan, B.S., Ed., New York: Wiley, 1972, vol. 2, p. 4.
Tolstikov, G.A., Tsypysheva, I.P., Kunakova, A.M., and Valeev, F.A., Izv. Ross. Akad. Nauk, Ser. Khim., 2001, p. 1618.
Pretsch, E., Clerc, T., Seibl, I., and Simon, W., Tables of Spectral Data for Structure Determination of Organic Compounds, Berlin: Springer, 1983, vol. 55, p. 71.
Steric Effects in Organic Chemistry, Newman, M.S., Ed., New York: Wiley, 1956. Translated under the title Prostranstvennye effekty v organicheskoi khimii, Moscow: Inostrannaya Literatura, 1960, p. 101.
March, J., Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, New York: Wiley, 1985. Translated under the title Organicheskaya khimiya, Moscow: Mir, 1987, vol. 2, p. 42.
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Valeev, F.A., Tsypysheva, I.P., Kunakova, A.M. et al. Functionalization of the Allyl Fragment in (+)-δ-Cadinol. Russian Journal of Organic Chemistry 40, 337–345 (2004). https://doi.org/10.1023/B:RUJO.0000034967.56553.3e
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DOI: https://doi.org/10.1023/B:RUJO.0000034967.56553.3e