Optically active seleninamides: isolation, absolute configuration, and racemization mechanism.
Optically active seleninamides were obtained for the first time by chromatographic resolution on an optically active column. The absolute configurations of the optically active seleninamides were determined by comparing their chiroptical properties with those of analogous sulfinamides, the stereochemistry of which was determined by transformation into chiral sulfoxides of known configurations. The optically active seleninamides were found to racemize in solution. Kinetic studies of the racemization and theoretical studies clarified that the racemization of the optically active seleninamides in solution proceeds via hypervalent hydrates formed by the reaction with water.
Nakashima
Yusuke
Y
Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University, Minami-ohsawa, Hachioji, Tokyo 192-0397, Japan.
Shimizu
Toshio
T
Hirabayashi
Kazunori
K
Kamigata
Nobumasa
N