Abstract:
The acid‐catalysed rearrangement of 3β, 16β‐dihydroxyandrost‐5‐en‐17‐one to 3β, 17β‐dihydroxyandrost‐5‐en‐16‐one was studied by 13C NMR spectroscopy. The spectra indicated that the reaction is produced by an intramolecular 1, 2‐shift of hydride from C‐16α to C‐17α. Copyright © 1988 John Wiley & Sons, Ltd.
Registro:
Documento: |
Artículo
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Título: | 13C NMR spectroscopic study of the rearrangement of 16β‐hydroxy‐17‐oxo steroids to 17β‐hydroxy‐16‐oxo isomers |
Autor: | Doller, D.; Gros, E.G. |
Filiación: | Departmento de Química Orgánica Y Umymfor, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Buenos Aires, 1428, Argentina
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Palabras clave: | 13C NMR spectra; 3β, 16β‐Dihydroxy‐androst‐5‐en‐17‐one; 3β, 17β‐Dihydroxy‐androst‐5‐en‐16‐one; Acid‐catalysed rearrangement |
Año: | 1988
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Volumen: | 26
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Número: | 7
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Página de inicio: | 539
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Página de fin: | 541
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DOI: |
http://dx.doi.org/10.1002/mrc.1260260702 |
Título revista: | Magnetic Resonance in Chemistry
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Título revista abreviado: | Magn. Reson. Chem.
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ISSN: | 07491581
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07491581_v26_n7_p539_Doller |
Referencias:
- Seldes, A.M., Anding, C.A., Gros, E.G., (1980) Steroids, 36, p. 575
- Seldes, A.M., Gros, E.G., (1982) Steroids, 39, p. 181
- Oka, K., Hara, S., (1978) J. Org. Chem., 43, p. 4408
- Doller, D., Gros, E.G., ; Kirk, D.N., Hartshorn, M.P., (1968) Steroid Reaction Mechanisms, p. 388. , Elsevier, Amsterdam
- Collins, C.J., Eastham, J.F., (1966) The Chemistry of Carbonyl Compounds, pp. 761-794. , edited by, S. Patai, Chapt. 15, pp., Interscience, New York
- Lowry, T.H., Richardson, K.S., (1981) Mechanism and Theory in Organic Chemistry, pp. 436-438. , 2nd ed., Harper and Row, New York
- Numazawa, M., Nagaoka, M., (1982), p. 530. , J. Chem. Soc., Chem. Commun; Wehrli, F.W., Wirthlin, T., (1980) Interpretation of Carbon‐13 NMR Spectra, pp. 107-110. , Heyden, London
- Johnson, W.S., Gastambide, B., Pappo, R., (1957) J. Am. Chem. Soc., 79, p. 1991
- Leeds, N.S., Fukushima, D.K., Gallagher, T.F., (1954) J. Am. Chem. Soc., 76, p. 2943
- Kincl, F.A., (1976) J. Steroid Biochem., 7, p. 419
Citas:
---------- APA ----------
Doller, D. & Gros, E.G.
(1988)
. 13C NMR spectroscopic study of the rearrangement of 16β‐hydroxy‐17‐oxo steroids to 17β‐hydroxy‐16‐oxo isomers. Magnetic Resonance in Chemistry, 26(7), 539-541.
http://dx.doi.org/10.1002/mrc.1260260702---------- CHICAGO ----------
Doller, D., Gros, E.G.
"13C NMR spectroscopic study of the rearrangement of 16β‐hydroxy‐17‐oxo steroids to 17β‐hydroxy‐16‐oxo isomers"
. Magnetic Resonance in Chemistry 26, no. 7
(1988) : 539-541.
http://dx.doi.org/10.1002/mrc.1260260702---------- MLA ----------
Doller, D., Gros, E.G.
"13C NMR spectroscopic study of the rearrangement of 16β‐hydroxy‐17‐oxo steroids to 17β‐hydroxy‐16‐oxo isomers"
. Magnetic Resonance in Chemistry, vol. 26, no. 7, 1988, pp. 539-541.
http://dx.doi.org/10.1002/mrc.1260260702---------- VANCOUVER ----------
Doller, D., Gros, E.G. 13C NMR spectroscopic study of the rearrangement of 16β‐hydroxy‐17‐oxo steroids to 17β‐hydroxy‐16‐oxo isomers. Magn. Reson. Chem. 1988;26(7):539-541.
http://dx.doi.org/10.1002/mrc.1260260702