Résumé
Par l'étude des rotations optiques, des spectres de l'ultraviolet, et des modèles moléculaires des alcaloides de l'aporphine, il a été démontré que dans les aporphines substituées en positions 4 et 5 le système biphényl est rigide et tordu.
References
Unless otherwise indicated these values were obtained fromR. H. F. Manske, The Alkaloids (Ed. byR. H. F. Manske andH. C. Holmes, Academic Press Inc., New York, N. Y. 1954), p. 119.
C. Yunusov andH. H. Progressov, Zhur. Obshchei Khim.20, 1151 (1950).
H. R. Arthur andH. T. Cheung, J. chem. Soc.,1959, 2306.
A. Ruegger, Helv. chim. Acta42, 754 (1959).
M. Tomita andF. Kusuda, Pharm. Bull., Japan1, 6 (1953).
T. Nakano, Pharm. Bull. Japan2, 333 (1954).
E. Schlittler andA. Lindenmann, Helv. chim. Acta32, 1880 (1949).
T. R. Govindachari andB. R. Pai, J. org. Chem.18, 1352 (1953).
M. Tomita andT. Kikuchi, Pharm. Bull., Japan3, 100 (1955).
An interesting observation made in the course of comparing ultra-violet values is that if both positions 3 and 4 are unsubstituted, such as in xylopine, stephanine, and crebanine, the peak in the 303–310 mµ region shifts to the 310–320 mµ region, and appears only as a shoulder.
S. Goodwin, J. N. Shoolery, andL. F. Johnson, Proc. chem. Soc.1958, 306.
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Shamma, M. The conformation of 4.5-substituted aporphine alkaloids. Experientia 16, 484–485 (1960). https://doi.org/10.1007/BF02158347
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DOI: https://doi.org/10.1007/BF02158347