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Chemical behavior of conjugated polyenoic acids toward sulfuric acid. acid-catalyzed cyclization and successive rearrangement ofTrans-β-ionylidene crotonic acid

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  • Chimica, Biochimica
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Zusammenfassung

Es wird eine neuartige, säurekatalysierte Zyklisierung und Umlagerung an einer konjugierten Tetraencarbonsäure beschrieben.

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References

  1. K. Tsukida, M. Ito andF. Ikeda, Experientia29, 1338 (1973).

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  2. Prepared according to (a); mp. 157° (from acetone), UV 319 nm (EtOH), characterized by IR, NMR, and MS. a)I. Heilbron, E. R. H. Jones andD. G. O'Sullivan, J. chem. Soc.,1946, 866; b)K. Eiter, E. Truscheit andH. Oediger, Angew. Chem.72, 948 (1960).

  3. No successful separation was effected on ordinary chromatographic columns, TLC plates, or by distillation.

  4. Pglc: 1.5% OV-17/Shimalite W, column 10′×3/8″, injector 215°, column 170°, detector 235°, He 150 ml/min. Glc: 1.5% OV-17/Shimalite W, 4 mm×1 m, 170°, 140°, 200°, N2 60 ml/min.

  5. UV-spectra were taken in ether, and NMR in CCl4 solutions.

  6. K. Tsukida, M. Ito andF. Ikeda, Chem. Pharm. Bull.21, 248 (1973).

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  7. T. S. Sorensen, Can. J. Chem.42, 2768 (1964).—M. Kuzuya andH. Hart, Tetrahedron Lett.1973, 4202.

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Authors and Affiliations

  1. Kobe Women's College of Pharmacy, Motoyama-kitamachi, Higashinada-ku, 658, Kobe, Japan

    K. Tsukida, M. Ito & F. Ikeda

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  1. K. Tsukida
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  2. M. Ito
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  3. F. Ikeda
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Tsukida, K., Ito, M. & Ikeda, F. Chemical behavior of conjugated polyenoic acids toward sulfuric acid. acid-catalyzed cyclization and successive rearrangement ofTrans-β-ionylidene crotonic acid. Experientia 30, 980–982 (1974). https://doi.org/10.1007/BF01938957

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  • DOI: https://doi.org/10.1007/BF01938957

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