ISSN:
0030-4921
Keywords:
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of optically active (1R,2R)- and (1S,2R)-2-deuterio-2,3-dihydro-2-methyl-6-nitrobenzothiophene-1-oxide (3 and 4) is described. Several racemic aryl methyl carbinols in the presence of 3 or 4 give different chemical shifts for enantiomeric CH, CH3 and OH protons. These chemical shift differences are larger than those observed in analogous sulfoxide-alcohol pairs without nitro groups. Quinine and cinchonidine cause observable non-equivalence of methylene and aromatic protons in racemic 4. The magnitude of the diastereomeric shift difference is sensitive to temperature, solvent, concentration, nature of the π system and steric effects.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1270220902
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