Optically active seleninate esters: isolation, absolute configuration, racemization mechanism, and transformation into chiral selenoxide.

摘要: Optically active seleninate esters were obtained for the first time by chromatographic resolution on an optically column. The absolute configurations of determined comparing their chiroptical properties with those two analogous sulfinate esters, configuration one which is known and that other was X-ray crystallographic analysis. found to racemize in solution. Kinetic studies racemization, oxygen exchange reaction H218O, theoretical clarified racemization solution proceeded via achiral hypervalent selenurane intermediate formed water. ester having bulky substituents Grignard reagents proceed retention stereochemistry give selenoxide...