Abstract
Syntheses are reported far sterically hindered 2-substituted benzodioxane analogs of isoflavone. An optically active lanthanide shift reagent (LSR) was used to show that these products exist as mixtures of atropoisomers. The difference in the chemical shifts of the enantiomeric protons in the presence of the LSR may reach 2–3 ppm with decreasing temperature. Conclusions were drawn concerning the structure of the LSR-substrate adducts and their conformations.
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References
N. V. Gorbulenko and V. P. Khilya, Ukr. Khim. Zh.,60, No. 1, 709 (1994).
A. L. Kazakov, V. P. Khilya, V. V. Mezheritskii, and D. Litkei, Natural and Modified Isoflavonoids [in Russian], Izd. Rostovsk. Univ., Rostov-on-the-Don (1985).
L. Carollini and G. Lucchetti, Gazz. Med. Ital.,135, Nos. 7-8, 365 (1976).
A. V. Turov, I. V. Komarov, V. P. Khilya, and M. Yu. Kornilov, Teor. Éksperim. Khim., No. 5, 629 (1989).
A. V. Turov and V. P. Khilya, Khim. Geterotsikl. Soedin., No. 6, 723 (1996).
B. Bleany, J. Magn. Reson.,8, 91 (1972).
M. Yu. Kornilov, A. V. Turov, and V. I. Zamkovoi, Ukr. Khim. Zh.,41, No. 7, 769 (1975).
H. M. McConnel and R. E. Robertson, J. Chem. Phys.,29, No. 12, 1361 (1958).
M. Yu. Kornilov, V. V. Plakhotnik, A. V. Turov, and V. P. Khilya, Ukr. Khim. Zh.,58, No. 11, 1026 (1992).
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Taras Shevchenko Kiev University, 252033 Kiev. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 902–908, July, 1996. Original article submitted March 27, 1996.
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Bondarenko, S.P., Turov, A.V. & Khilya, V.P. Synthesis of sterically hindered benzodioxane analogs of isoflavone and a study of their atropoisomerism. Chem Heterocycl Compd 32, 767–772 (1996). https://doi.org/10.1007/BF01165717
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DOI: https://doi.org/10.1007/BF01165717