Considerable study of
alkoxysilanes as intramolecular hydrogen transfer agents has
been undertaken.The di-t-butyloxysilanes, prepared from di-tbutylchlorosilane
and the requisite alcohol, are particularly effective
and are generally stable to column chromatography.
Treatment of a γ-iodoallylic alcohol with NaH and t-Bu2SiHCl
afforded the corresponding di-t-butyloxysilanes which were exposed
to UV irradiation in the presence of 10% hexabutylditin
in the so-called unimolecular chain transfer (UMCT) reaction of
silicon hydrides to afford the reduced alkene (eq 1）.
