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Stereochemical study of hexahydro[1,3]thiazolo[3,2-a]pyridines by 1H and 13C NMR

✍ Scribed by Didier Barbry; Guy Ricart; Daniel Couturier

Publisher
John Wiley and Sons
Year
1981
Tongue
English
Weight
625 KB
Volume
17
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Configurations and preferred conformations of a number of hexahydro[1,3]thiazolo[3,2‐a]pyridines have been assigned on the basis of their ^1^H and ^13^C NMR spectra. The conformational preferences of these compounds have been interpreted in terms of the minimization of dipolar type interactions, arising from 1,3 arrangements of the heteroatoms, which are increased by the electron donor induction effect of the alkyl groups. The stereochemistry of the salts of these bases is very different from that of the free compounds. For the gem‐disubstituted compound, an explanation in terms of the ‘gem‐dimethyl effect’ and a slight deformation at the nitrogen atom is proposed.

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