The presence of the bulky t-butyl
groups in di-t-butyldichlorosilane has been found to increase the
Si–C bond lengths slightly and to widen the CSiC bond angles by
11.1? relative to dichlorodimethylsilane as determined by electron
diffraction and molecular mechanics calculations.
The di-t-butylsilylene protecting group for diols was introduced
by Trost and Caldwell and used in a total synthesis of
deoxypillaromycinone.It is introduced by the reaction of di-tbutyldichlorosilane
with a 1,2- or 1,3-diol in acetonitrile in the
presence of triethylamine and 1-hydroxybenzotriazole (HOBt)
at 45–90°C (eq 1). For a related, highly reactive reagent see
di-t-butylsilyl Bis(trifluoromethanesulfonate).
