Interhalogen-Catalyzed Cleavages of Ethers and Esters with Trimethylsilyl Bromide or Chloride

Article abstract of DOI:10.1021/jo00158a018

The cleavages of various dialkyl ethers, trimethylsilyl alkyl ethers, and alkyl esters by trimethylsilyl bromide are strongly catalyzed by iodine monobromide.This catalyzed cleavage procedure using iodine monobromide makes possible synthetic applications for trimethylsilyl bromide which were previously ruled out by problems with its low reactivity.Cleavages of benzylic and tertiary alkyl ethers and esters by trimethylsilyl chloride are feasible when catalyzed by iodine monochloride.However, other systems are essentially unreactive toward trimethylsilyl chloride even in the presence of iodine monochloride.