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Stereoselectivity in quaternization of thebaine. 270 MHz PMR spectroscopic studies

Manoharan, Samuel T and Madhyastha, Madhava K (1987) Stereoselectivity in quaternization of thebaine. 270 MHz PMR spectroscopic studies. In: Indian Journal of Chemistry, 26B (2). pp. 140-142.

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Abstract

The quaternization of thebaine (I) with Pr iodide and iso-Pr iodide was studied by PMR spectroscopy. The results indicate that the major diastereomer is formed to the extent of approximate 75% of the diastereomeric mixture by axial attack of the alkyl halide. There is no significant change in the ratio of the diastereomers with solvent or with large excess of the alkyl halide used. The diastereomers were separated by column chromatog. on neutral alumina, characterized by various phys. data and the configuration at the quaternary nitrogen assigned on the basis of PMR spectra (270 MHz). The stereoselectivity in quaternization further proved by reverse quaternization.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to National Institute of Science Communication and Information Resources.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 13 Jun 2008
Last Modified: 27 Aug 2008 13:26
URI: http://eprints.iisc.ernet.in/id/eprint/14268

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