The configuration of β-eucaine and β-isoeucaine
- 1 May 1967
- journal article
- Published by Oxford University Press (OUP) in Journal of Pharmacy and Pharmacology
- Vol. 19 (5) , 318-321
- https://doi.org/10.1111/j.2042-7158.1967.tb08093.x
Abstract
The configurations of the two isomers, β-eucaine (benzamine hydrochloride B.P.C. 1954) and β-isoeucaine have been deduced. As a result of a study of the nuclear magnetic resonance spectra and of catalytic hydrogenation and oxidation, the α-form has been assigned an equatorial hydroxyl group on C-4 and the β-form an axial hydroxyl group in this position.Keywords
This publication has 11 references indexed in Scilit:
- 627. Proton magnetic resonance in some substituted epimeric piperidin-4-olsJournal of the Chemical Society, 1965
- Communications - Conformational Study of 1,2,-2,6,6-Pentamethyl-4-Phenyl-4-PiperidinolThe Journal of Organic Chemistry, 1957
- Observations on the Stereochemistry of BenzamineJournal of Pharmacy and Pharmacology, 1954
- Stereochemistry of CocaineNature, 1954
- Beweis der Konfiguration des Pseudo‐tropins, bzw. des TropinsHelvetica Chimica Acta, 1953
- 150. The stereochemistry of the tropane alkaloids. Part I. The configuration of tropine and ψ-tropineJournal of the Chemical Society, 1953
- Configuration of Tropine and PseudotropineJournal of the American Chemical Society, 1952
- Stereochemistry of the Tropane AlkaloidsNature, 1952
- VII.—Stereoisomerism and local anœsthetic action in the β-eucaine group. Resolution of β- and iso-β-eucaineJournal of the Chemical Society, Transactions, 1924
- Ueber stereochemische Untersuchungen in der PiperidinreiheEuropean Journal of Organic Chemistry, 1897