Carbonyl compounds iodotrimethylsilane

Acetaliziation and aUylation of carbonyl compounds Iodotrimethylsilane is an effective catalyst for acetalization with an alkoxysilane. Addition of allyltrimethylsilane to this reaction results in allylation of the acetal to form a homoallyl ether. 

Cleavage of ethers. The actual reagent formed from these two reagents is believed to be iodotrichlorosilane and is similar to iodotrimethylsilane for cleavage of ethers but somewhat more regioselective. It also cleaves acetals and ketals quantitatively to the carbonyl compound at room temperature. 

At the end of his review [7] dealing with the acetalization of carbonyl compounds, Sakurai reported a previously unpublished observation. In the presence of catalytic amounts of iodotrimethylsilane and one equivalent of tetramethoxysilane 38, allyl-trimethylsilane 1 underwent smooth condensation with benzaldehyde 39, leading to adduct 41 in good yield. The silyl-modified Sakurai reaction was born (Scheme 13.15). 

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