The first example of racemization of the sulfur stereogenic center of α-sulfinyl carbanions at low temperatures

The treatment of enantiopure aryl dichloromethyl sulfoxides in THF with strong bases such as LDA, LiHMDS, NaHMDS, and KHMDS resulted in racemization of the sulfur stereogenic center of the sulfoxides even at ?78 °C. The rate of the racemization was found to be dependent on the alkali metal of the bases used. This is the first example of the racemization of the sulfur stereogenic center of α-sulfinyl carbanions at low temperatures.