Abstract
RL-Inversion of chiral spirocyclic and open-chain 2-arylaminotropone derivatives with varied heteroatom (O, S, N) has been studied. Kinetic relations holding in the RL-permutation are discussed. Its mechanism includes formation and dissociation of spiro bonds and torsion stereodynamics.
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REFERENCES
Kurbatov, S.V., Budarina, Z.N., Borisenko, N.I., Vaslyaeva, G.S., Knyazev, A.P., Olekhnovich, L.P., and Zhdanov, Yu.A., Russ. J. Org. Chem., 1999, vol. 35, no. 11, pp. 1683-1688.
Olekhnovich, L.P., Budarina, Z.N., Lesin, A.V., Kurbatov, S.V., Borodkin, G.S., and Minkin, V.I., Mendeleev Commun., 1994, no. 2, pp. 162-165.
Furmanova, N.G., Olekhnovich, L.P., Minkin, V.I., Struchkov, Yu.T., Kompan, O.E., and Budarina, Z.N., Zh. Org. Khim., 1982, vol. 18, no. 3, pp. 474-484.
Olekhnovich, L.P., Kurbatov, S.V., Budarina, Z.N., Minkin, V.I., and Zhdanov, Yu.A., Zh. Org. Khim., 1985, vol. 21, no. 12, pp. 2550-2555.
Kurbatov, S.V., Budarina, Z.N., Olekhnovich, L.P., Furmanova, N.G., Lesin, A.V., Kompan, O.E., Min-kin, V.I., and Zhdanov, Yu.A., Zh. Org. Khim., 1988, vol. 24, no. 5, pp. 913-922.
Knyazev, V.N. and Drozd, V.N., Russ. J. Org. Chem., 1995, vol. 31, no. 1, pp. 1-26; Terrier, F., Chem. Rev., 1982, vol. 82, no. 2, pp. 77–152; Strauss, M.J., Chem. Rev., 1970, vol. 70, no. 3, pp. 667–712.
Eaton, S.S. and Holm, R.H., Inorg. Chem., 1970, vol. 10, pp. 1446-1452.
Olekhnovich, L.P., Kurbatov, S.V., Lesin, A.V., Budarina, Z.N., Zhdanov, Yu.A., and Minkin, V.I., Zh. Org. Khim., 1991, vol. 27, no. 1, pp. 6-13.
Tsai, C.J. and Jordan, K.D., J. Phys. Chem., 1993, vol. 97, no. 8, pp. 1127-1137.
Weygand–Hilgetag organisch-chemische Experi-mentierkunst, Hilgetag, G. and Martini, A., Eds., Leipzig: Johann Ambrosius Barth, 1964, 3rd ed. Translated under the title Metody eksperimenta v organicheskoi khimii, Moscow: Khimiya, 1968, pp. 197, 230.
Minus, R.A., Elliot, A.J., and Sheppard, W.A., Org. Synth., 1977, vol. 57, no. 1, pp. 117-121.
Forbes, C.E. and Holm, R.H., J. Am. Chem. Soc., 1968, vol. 90, no. 12, p. 6884.
Fieser, L.F. and Fieser, M., Reagents for Organic Synthesis, New York: Wiley-Intersci., vol. 1, 1967. Translated under the title Reagenty dlya organiche-skogo sinteza, Moscow: Mir, 1970, vol. 3, p. 459.
Soma, N., Nakazawa, G., Watanabe, T., Sato, Y., and Sunagawa, G., Chem. Pharm. Bull., 1965, vol. 13 (4), no. 3, pp. 457-464.
Soma, N., Nakazawa, G., Watanabe, T., Sato, Y., and Sunagawa, G., Chem. Pharm. Bull., 1965, vol. 13 (7), no. 5, pp. 819-828.
Metody polucheniya khimicheskikh reaktivov i pre-paratov (Methods of Synthesis of Chemical Reagents and Preparations), Moscow: IREA, 1971, vol. 23, pp. 150-152.
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Olekhnovich, L.P., Budarina, Z.N., Borodkin, G.S. et al. Acylotropic Tautomerism: XXXV. RL-Inversion of Configuration of Dipolar Spyrocyclic and Open-Chain 2-Arylaminotropone Isomers. Russian Journal of Organic Chemistry 38, 713–722 (2002). https://doi.org/10.1023/A:1019619307779
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DOI: https://doi.org/10.1023/A:1019619307779