Premium
Magnetic resonance study of diastereomeric interactions of nitroaromatic sulfxides with alcohols in solution
Author(s) -
Sweeting Linda M.,
Anet Frank A. L.
Publication year - 1984
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.1270220902
Subject(s) - diastereomer , chemistry , enantiomer , chemical shift , steric effects , methylene , medicinal chemistry , alcohol , solvent , sulfoxide , aryl , nitro , atropisomer , stereochemistry , organic chemistry , alkyl
The synthesis of optically active (1 R ,2 R )‐ and (1 S ,2 R )‐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, CH 3 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.