1,3-Bis(triisopropylsilyl)propyne is a precursor of a stereoselective bulky C3 nucleophile, functionalized
Peterson reagent.
The main use of the title reagent is as a precursor of the
lithium derivative. 1,3-Bis(triisopropylsilyl)propyne is cleanly
lithiated by treatment with equiv of n-butyllithium in THF at
?20°C (15 min) to what is probably an equilibrium mixture of
propargylic and allenic species (1) and (2) (eq 1).The bulky
triisopropylsilyl (TIPS) group serves as a controlling group in the
addition of (1/2) to electrophiles.
