Abstract
13C-Nuclear magnetic resonance spectra of a series of di-isophorone derivatives have been mapped and the individual resonances assigned. Assignments were obtained by comparing and correlating the spectra of closely related di-isophorones of known structure. Estimates, based on approximate calculations, of the chemical shifts of the six methylene moieties of the di-isophorone skeleton are in fair agreement with the observed values.
Zusammenfassung
Die13C-Kernresonanzspektren einer Reihe von Di-isophoron-Derivaten wurden gemessen und die Signale den einzelnen Kohlenstoffatomen zugeteilt. Die Zuordnung erfolgte auf Grund des Vergleichs von Spektren verwandter Di-isophorone bekannter Struktur. Für die Resonanzen der Ringmethylen-Gruppen wurde eine befriedigende Übereinstimmung der gefundenen Werte mit errechneten Schätzungswerten festgestellt.
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Part 9.Allen A. A., Kurzer F., Monatsh. Chem.112, 769 (1981).
For a preliminary note, seeMorgan A. R.,Kapadia Z.,Davies P. R.,Kurzer F., Chem. Indust. (London)1980, 789.
Johnson L. F., Jankowski W. C., Carbon-13 NMR Spectra. A Collection of Assigned Coded and Indexed Spectra. New York: Wiley-Interscience. 1972;Shamma M., Hindenlang D. M., Carbon-13 NMR Shift Assignments of Amines and Alkaloids. New York: Plenum Press. 1979.
Stothers J. B., Carbon-13 NMR Spectroscopy. New York: Academic Press. 1972.
Levy G. C., Nelson G. L., Carbon-13 Nuclear Magnetic Resonance for Organic Chemists. New York: Wiley-Interscience. 1972.
Wehrli F. W., Wirthlin T., Interpretation of Carbon-13 NMR Spectra. London: Heyden & Son Ltd. 1976.
Reich H. J., Jautelat M., Messe M. T., Weigert F. J., Roberts J. D., J. Amer. Chem. Soc.91, 7445 (1969).
Eggert H., Djerassi C., J. Org. Chem.38, 3788 (1973);Eggert H., Van Antwerp C. L., Bhacca N. S., Djerassi C., ibid.41, 71 (1976).
ApSimon J. W., Beierbeck H., Saunders J. K., Canad. J. Chem.51, 3874 (1973);Hansen J. R., Siverns M., J. Chem. Soc. Perkin I1975, 1110; ibid.1975, 1956.
Davies P. R., M. Phil. Thesis, London 1980.
Morgan A. R., Ph.D. Thesis, London 1979.
The nomenclature that was originally adopted continues to be employed [cf.Allen A. A., Duffner R. C., Kurzer F., Tetrahedron34, 1247 (1978)].
Wenkert E., Buckwalter B. L., J. Amer. Chem. Soc.94, 4367 (1972).
Buckwalter B. L., Burfitt I. R., Nagel A. A., Wenkert E., Naf F., Helv. Chim. Acta58, 1567 (1975).
Bertrand J. A., Cheung D., Hammerich A. D., House H. O., Reichle W. T., Vanderveer D., Zaiko E. J., J. Org. Chem.47, 1600 (1977).
Abraham R. J., Loftus P., Proton and Carbon-13 NMR Spectroscopy. London: Heyden & Son Ltd. 1978.
Allerhand A., Doddrell D., Komorski R., J. Chem. Phys.55, 189 (1971).
Dalling D. K., Grant D. M., J. Amer. Chem. Soc.89, 6612 (1967);Mason J., J. Chem. Soc. (A)1971, 1038.
Wahlberg I., Almquist S. O., Nishida T., Enzell C. R., Acta. Chem. Scand.29 B, 1047 (1975).
Roberts J. D., Weigert F. J., Kroschwitz J. I., Reich H. J., J. Amer. Chem. Soc.92, 1338 (1970).
Weigert F. J., Roberts J. D., J. Amer. Chem. Soc.92, 1347 (1970).
Pehk T., Lippmaa E., Eesti N. S. V. Tead, Akad. Toim Keem. Geol.17, 291 (1968).
Parker R. G., Roberts J. D., J. Amer. Chem. Soc.92, 743 (1970).
Burke J. J., Lauterbur P. C., J. Amer. Chem. Soc.86, 1870 (1964).
Lippmaa E., Pehk T., Eesti N. S. V. Tead, Akad. Toim Keem. Geol.17, 287 (1968).
Kabas G., Rutz H. C., Tetrahedron22, 1219 (1966).
Allen A. A.,Kurzer F.,Morgan A. R., J. Chem. Soc. Perkin I1980, 733.
Davies P. R., Kurzer F., Morgan A. R., Monatsh. Chem.111, 1097 (1980).
Furth B.,Kossanyi J.,Morizur J. P.,Vandewalle M., Bull. Soc. chim. France1967, 1428.
Allen A. A., Kurzer F., Tetrahedron34, 1261, 1267 (1978).
Kurzer F., Morgan A. R., Monatsh. Chem.112, 129 (1981).
Duffner R. C.,Kurzer F., unpublished results.
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Davies, P.R., Morgan, A.R. & Kurzer, F. Di-isophorone and related compounds. Part 1013C-nuclear magnetic resonance spectra of di-isophorone derivatives. Monatsh Chem 114, 739–751 (1983). https://doi.org/10.1007/BF01134186
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DOI: https://doi.org/10.1007/BF01134186