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Direct Conversion of Trimethylsilyl and Tetrahydropyranyl Ethers into Their Bromides and Iodides Under Neutral Conditions Using N-Bromo and N-Iodosaccharins in the Presence of Triphenylphosphine

H. Firouzabadi*, N. Iranpoor* and F. Ebrahimzadeh

Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454, Iran

Trimethylsilyl and tetrahydropyranyl ethers were easily converted into their corresponding bromides and iodides with high efficiency and selectivity by N-bromo- and N-iodosaccharins in the presence of triphenylphosphine under neutral conditions. The reaction of trimethyloctyloxysilane as a model compound was studied in different solvents with different ratios of silyl ethers, triphenylphosphine and N-halosaccharin at room temperature, in order to optimize the reaction conditions.

Keywords: Silyl and tetrahydropyranyl ethers, N-Bromosaccharin, N-Iodosaccharin, Triphenylphosphine, Bromide, Iodide