Optical resolution and racemization mechanism of a tellurinic acid.
[reaction: see text] Optically active tellurinic acid was obtained for the first time by chromatographic resolution of racemic 2,4,6-triisopropylbenzenetellurinic acid (1) using a chiral column. Optically active tellurinic acid (+)-1 was stable toward racemization in hexane, although racemization occurred in hexane/2-propanol. The kinetic studies for the racemization, oxygen exchange reaction using H(2)(18)O, and theoretical studies clarified that the racemization of the optically active tellurinic acid in solution proceeds via a hypervalent tellurane formed by addition of water remaining in solvent.
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
D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000032:analysis / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013691:Tellurium / Q000737:chemistry*
C495938:2,4,6-triisopropylbenzenetellurinic acid; D009942:Organometallic Compounds; D013691:Tellurium