Author Topic: Robinson-Schöpf reaction: tropinone  (Read 1384 times)

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Megatherium

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Robinson-Schöpf reaction: tropinone
« on: May 17, 2003, 06:35:00 PM »
Here are a few refs. for the Robinson-Schöpf reaction, involving the synthesis of tropinones from a dialdehyde, methylamine and acetonedicarboxylic acid:

R. Robinson, J. Chem. Soc. (1917) vol 111, p 762, 876
C. Schöpf, Angew. Chem. (1937) vol. 50, p 779, 797
K. Alder et al., Ann. (1956) vol. 601, p 147
R. D. Guthrie, J. F. McCarthy, J. Chem. Soc. (1967), p 62
R. V. Stevens, A. W. M. Lee, J. Am. Chem. Soc. (1979) vol. 101, p 7032
M. Langlois et al., Synth. Commun. (1992) vol 22, p 3115
T. Jarevang et al., Acta Chem. Scand. (1998) vol 52, p 1350

Mechanism:

http://holivo.pharmacy.uiowa.edu/reaction/robinson.pdf



The synthesis of acetonedicarboxylic acid from citric acid can be found in Organic Syntheses, CV 1, 10