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Stereochemical study of hexahydro[1,3]thiazolo[3,2‐ a ]pyridines by 1 H and 13 C NMR
Author(s) -
Barbry Didier,
Ricart Guy,
Couturier Daniel
Publication year - 1981
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270170206
Subject(s) - chemistry , heteroatom , nitrogen atom , stereochemistry , alkyl , nmr spectra database , carbon 13 nmr , chemical shift , computational chemistry , spectral line , organic chemistry , physics , astronomy
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.