Summary
In the course of an attempted elimination reaction starting from an isothiochromane derivative substituted with an amino-alcohol moiety, a benzo[c]thiophene derivative formed via a rearrangement reaction was isolated unexpectedly. Its constitution was confirmed unambiguously via17O-NMR-spectroscopy.
Zusammenfassung
Im Verlauf einer versuchten Eliminierungstreaktion wurde ausgehend von einem Aminoalkoholderivat eines Isothiochromansystems unerwarteterweise ein Benzo[c]thiophen-derivat isolert. Die Konstitution des Umlagerungsproduktes wurde eindeutig durch17O-NMR-Spektroskopie bestätigt.
Similar content being viewed by others
References
Fröhlich J., Ilk R., Robien W., Kählig H. P. (1991)17O-NMR-Spectroscopy of Heterocyclic Spiro-Compounds and Their Precursors (Poster presented at the Jahrestagung der Fachgruppe Magnetische Resonanz der GdCh, Sep. 29–Oct. 2, 1991, Todtmoos, Germany)
Ilk R. (1991) PhD-Thesis. Technical University, Vienna; Fröhlich J., Ilk R., Sauter F. (in preparation)
Pretsch E., Seibl J., Clerc Th., Simon W. (1981) Tabellen zur Strukturaufklärung organischer Verbindungen. Springer, Berlin-Heidelberg-New York
General information on applications of17O-NMR-spectroscopy: Boykin D. W. (1991)17O-NMR-Spectroscopy in Organic Chemistry. CRC Press, Boca Raton
Boykin D. W. (1991)17O-NMR-Spectroscopy in Organic Chemistry. CRC Press, Boca Raton, pp. 171, 173
Kalabin G. A., Kushnarev D. F., Valeyev R. B., Trofimov B. A., Fedotov M. A. (1982) Org. Magn. Reson.18: 1
Eliel E. L., Pietrusiewicz K. M., Jewell L. M. (1979) Tetrahedron Lett.1979: 3649
Boykin D. W. (1991)17O-NMR-Spectroscopy in Organic Chemistry. CRC Press, Boca Raton, pp. 147f
Fröhlich J. L. et al. (unpublished results)
Boykin D. W. (1991)17O-NMR-Spectroscopy in Organic Chemistry. CRC Press, Boca Raton, p. 143
Hofmann H., Salbeck G. (1969) Ang. Chem. Int. Ed.8: 456
Rane D. F., Pike R. E., Puar M. S., Wright J. J., McPhail A. T. (1988) Tetrahedron44: 2397
Kalchhauser H., Robien W. (1985) J. Chem. Inform. Comput. Sci.25: 103
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Fröhlich, J., Ilk, R., Kählig, H. et al. Elucidation of the constitution of a heterocyclic rearrangement product by means of17O-NMR-spectroscopy. Monatsh Chem 124, 1195–1200 (1993). https://doi.org/10.1007/BF00810028
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00810028