Abstract
Hydrolysis of allyl carbinol oxides in aqueous HClO4 gave the corresponding 1,2,4-triols. On heating in the same reaction medium, they underwent cyclization into 3-hydroxytetrahydrofurans. The method is restricted to substrates that can generate stable carbocations via elimination of the hydroxy group from position 4 in intermediate 1,2,4-triols.
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References
A. A. Semenov, Ocherk khimii prirodnykh soedinenii [An Outline of the Chemistry of Natural Compounds], Nauka, Novosibirsk, 2000, 298 pp. (in Russian).
M. D. Mashkovskii, Lekarstvennye sredstva [Drugs], OOO “Izdatel’stvo Novaya Volna”, Moscow, 2001, 1, 2 (in Russian).
R. C. Larock, Comprehensive Organic Transformations. A Guide to Functional Group Preparations, Wiley, Inc., 1999, p. 905.
M. V. Chirskaya, A. A. Vasil’ev, N. L. Sergovskaya, S. V. Shorshnev, and S. I. Sviridov, Tetrahedron Lett., 2004, 45, 8811.
M. Karikomi, S. Watanabe, Y. Kimura, and T. Uyehara, Tetrahedron Lett., 2002, 43, 1495.
A. Bhaumik and T. Tatsumi, Chem. Commun., 1998, 463.
Y. Okimoto, D. Kikuchi, S. Sakaguchi, and Y. Ishii, Tetrahedron Lett., 2000, 41, 10223.
N. A. Petasis and S.-P. Lu, J. Am. Chem. Soc., 1995, 117, 6294; (b) O. Andrey, L. Ducry, Y. Landais, D. Planchenault, and V. Weber, Tetrahedron, 1997, 53, 4339; (c) M. A. Ciufolini, M. V. Deaton, S. Zhu, and M. Chen, Tetrahedron, 1997, 53, 16299; (d) F. Lacrampe, F. Leost, and A. Doutheau, Tetrahedron Lett., 2000, 41, 4773.
A. Murai, M. Ono, and T. Masamune, Bull. Chem. Soc. Jpn, 1977, 50, 1226; (b) J.-P. Bats, J. Moulines, P. Picard, and D. Leclercq, Tetrahedron, 1982, 38, 2139; (c) R. D. Evans, J. W. Magee, and J. H. Schauble, Synthesis, 1988, 862.
B. H. Lipshutz and J. C. Barton, J. Am. Chem. Soc., 1992, 114, 1084; (b) E. D. Mihelech and G. A. Hite, J. Am. Chem. Soc., 1992, 114, 7318; (c) S. B. Bedford, K. E. Bell, G. Fenton, C. J. Hayes, D. W. Knight, and D. Shaw, Tetrahedron Lett., 1992, 33, 6511; (d) J. M. Barks and D. W. Knight, Tetrahedron Lett., 1994, 35, 7259.
M. Tiecco, L. Testaferri, L. Bagnoli, R. Terlizzi, A. Temperini, F. Marini, C. Santi, and C. Scarponi, Tetrahedron: Asymmetry, 2004, 15, 1949.
R. F. Curtis, C. H. Hassal, and J. Weatherston, J. Chem. Soc., 1962, 4225; (b) Y. Kashman, I. Neeman, and A. Lifshitz, Tetrahedron, 1969, 25, 4617; (c) K. W. Gopinath and P. K. Mahanta, Tetrahedron, 1976, 32, 737.
P. Picard and J. Moulines, Bull. Soc. Chim. Fr., 1974, 2889.
Y. Ishibashi, S. Nishiyama, Y. Shizuri, and S. Yamamura, Tetrahedron Lett., 1992, 33, 521.
D. Wagner, V. L’vov, and A. Bening, Zh. Russ. Fiz.-Khim. O-va., 1904, 36, 539; (b) W. Reppe, Justus Liebigs Ann. Chem., 1955, 596, 113.
S. Ranganathan, R. Kumar, and V. Maniktala, Tetrahedron, 1984, 40, 1167; (b) M. P. Dreyfuss, J. Org. Chem., 1963, 28, 3269; (c) R. Kieffer, Bull. Soc. Chim. Fr., 1967, 3026; (d) G. A. Tolstikov, A. Yu. Spivak, S. I. Lomakina, and A. V. Kuchin, Izv. Akad. Nauk SSSR, Ser. Khim., 1985, 1109 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985, 34, 1012 (Engl.Transl.)].
F.-X. Felpin and J. Lebreton, J. Org. Chem., 2002, 60, 7353.
V. I. Pansevich-Kolyada, V. A. Ablova, and L. A. Kureichik, Zh. Obshch. Khim., 1955, 25, 2448 [J. Gen. Chem. USSR, 1955, 25 (Engl.Transl.)].
C. Ticozzi and A. Zanarotti, Tetrahedron Lett., 1994, 40, 7421; (b) A. Bachki, F. Foubelo, and M. Yus, Tetrahedron: Asymmetry, 1996, 7, 2997.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1252–1255, July, 2006.
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Chirskaya, M.V., Vasil’ev, A.A., Shorshnev, S.V. et al. Transformation of homoallylic alcohol oxides into 3-hydroxytetrahydrofurans in aqueous HClO4 . Russ Chem Bull 55, 1300–1303 (2006). https://doi.org/10.1007/s11172-006-0415-8
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DOI: https://doi.org/10.1007/s11172-006-0415-8