Configuration and conformation of all four cocaines from nmr spectra
- 1 January 1968
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 87 (9) , 1027-1041
- https://doi.org/10.1002/recl.19680870909
Abstract
The configurations of (±)‐allococaine and (±)‐allopseudococaine have been determined, for the first time in an unambiguous way, by means of NMR spectroscopy. The known configurations of (±)‐cocaine and (±)‐pseudococaine receive independent confirmation.The preferential conformation of the piperidine ring of the tropane nucleus is found to be the chair form in all four isomers, and also in the methyl esters of the four corresponding isomers of ecgonine.The preparation of (±)‐allococaine and (±)‐allopseudococaine has been improved.Keywords
This publication has 17 references indexed in Scilit:
- Conformational characterization of simple group VI heterocyclesJournal of the American Chemical Society, 1967
- A Direct, Qualitative Determination of Nonchair and Distorted-Chair Conformations of Six-Membered RingsJournal of the American Chemical Society, 1967
- 717. A proton resonance study of the conformations of carbohydrates in solution. Part I. Derivatives of 1,2-O-isopropylidene-α-D-xylo-hexofuranoseJournal of the Chemical Society, 1962
- The Proton Magnetic Resonance Spectra of Some α-Acetoxy KetonesJournal of the American Chemical Society, 1961
- Ranger Space Shot SlatedThe Science News-Letter, 1961
- Über das dritte racemische CocainEuropean Journal of Inorganic Chemistry, 1956
- Konfiguration des Cocains und Derivate der EcgoninsäureHelvetica Chimica Acta, 1955
- The structure of tropine-hydrobromideActa Crystallographica, 1954
- Conformation of Tropane AlkaloidsNature, 1953
- Review. La France glorieuse au moyen age. Aubert, M.French Studies, 1949