1,3-Bis(triisopropylsilyl)propyne

Physical properties

bp 130–135°C/0.08 mmHg; d 0.846 g cm?3.

Uses

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.

Application

1,3-Bis(triisopropylsilyl)propyne(1,3-bis(TIPS)propyne) is a precursor of a stereoselective bulky C3 nucleophile, functionalized Peterson reagent.

Preparation

1,3-bis(TIPS)propyne is prepared in quantitative yield by silylation of 3-lithio-1-triisopropylsilyl-1- propyne with triisopropylsilyl trifluoromethanesulfonate.

storage

1,3-Bis(triisopropylsilyl)propyne is no special precautions required; the reagent is not changed when stored for several months at ambient temperature. The Li derivative is handled under inert gas using simple syringe equipment.