Alkyl tert-butyl trimethylsilyl ether

Cleavage of Alkyl tert-Butyl Trimethylsilyl Ether. 258... 

Acylsulfenyl halides are formed by the reaction of N-bromosuccinimide or tert-butyl hypochlorite with thiocarboxylic acid O-trimethylsilyl esters164 (equation 172). Treatment of silyl carboxylates with triphenylphosphine dibromide gives the corresponding acyl bromide along with the silyl bromide165 (equation 173). It is also possible to convert silyl ethers to the alkyl bromide with this reagent165 or with a mixture of carbon tetrabromide and triphenylphosphine166. The mild nature and selectivity of the reaction is underscored by the conversion of the trimethylsiloxy /Mactam 83 to the bromide 84165 (equation 174). 

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