[89656-96-2] · C12H20SSi · 2-(Phenylthio)-2-(trimethylsilyl)propane · (MW 224.48)
Physical Data: bp 70-80 °C/0.6 mmHg.
Purification: by flash chromatography and by Kugelrohr distillation.3
Handling, Storage, and Precautions: use in a fume hood.
Reductive lithiation of 2-(phenylthio)-2-(trimethylsilyl)propane with Lithium 1-(Dimethylamino)naphthalenide (LDMAN) furnishes 2-lithio-2-(trimethylsilyl)propane, which is an intermediate for Peterson alkenation. The specific example in eq 1 features silicon-directed diene synthesis.1
m-Chloroperbenzoic Acid oxidizes 2-(phenylthio)-2-(trimethylsilyl)propane to the sulfone, which is then converted to the ketone via sila-Pummerer rearrangement (eq 2).3
Uko E. Udodong
Eli Lilly and Company, Indianapolis, IN, USA