The erythro-and three-amphetamine-B-d diastereomers were synthesized and used for the unambiguous assignment of the diastereotopic benzylic protons and the measurement of vicinal l~-l~ coupling constants which were used to determine the distribution of rotamers around the central co-c8 bond in the s
NMR assignment of diastereotopic protons in amphetamine by the use of Eu(fod)3
โ Scribed by G.E. Wright
- Publisher
- Elsevier Science
- Year
- 1973
- Tongue
- French
- Weight
- 98 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
In the ABX nmr spectra of amphetamines and related compounds, a problem arises in the assignment of individual A and B protons since usually there is no a priori reason to assign one "quartet" to one or the other of the diastereotopic protons.
(Suggestions have been made, however, that the A proton in (R)-amphetamines, as labelled in structures I and II, corresponds to the upfield signal in the nmr spectra of amphetamine hydrochlorides in deuterochloroform'.
๐ SIMILAR VOLUMES
Recently the use of two new shift reagents, Eu(fod)3 and Pr(fod)3, have been reported by Rondeau and Sievers. \* The advantage of these as shift reagents is due to their relatively high solubility in nonalcholic solvents and to the fact that neither Eu(fod)3
An assignment of relative configurations has been achieved for the diastereomeric racernates(lR2R,lS2S) and (1R2S, 1S2R) of 3,3-dimethyl-l,2-diphenylbuta~-l-ol through the comparative analysis of the respective chemical shifts induced by Eu(fod), in the 'H and '"C NMR spectra, and the corresponding