Preparation and stereochemical integrity of certain thioesters of 2-arylpropionic acids and related compounds.
2-Arylpropionate thioesters 5, 6a/6b and 7a/7b, 2-aryloxypropionate thioesters 8a/8b and 2-alkoxy-2-arylacetate thioesters 9a/9b were prepared from thiol 4 and the corresponding carboxylic acids. Thioesters 6a/6b, 7a/7b, 8a/8b and 9a/9b were monitored for evidence of inter-conversion between epimers in acetonitrile solvent at 40 degrees C, by optical activity in the cases of 6a/6b and 7a/7b, and by 1H NMR spectroscopy in the cases of 8a/8b and 9a/9b. Only in the case of thioesters 9a/9b was significant inter-conversion between epimers observed.
Hanrahan
Patrick E
PE
Department of Chemistry/Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland.
Moynihan
Humphrey A
HA
D004952:Esters; D009682:Magnetic Resonance Spectroscopy; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004952:Esters; D011422:Propionates