Silane/iodine-based cleavage of esters and ethers under neutral conditions

Abstract

New, efficient cleavage of carboxylic esters with iodotrimethylsilane or a mixture of phenyltrimethylsilane and iodine is described. Essentially neutral conditions can be maintained throughout the reactions. Ethers can be dealkylated by the latter method in high yields. The mechanism of the cleavage reactions is considered to include six-membered ring homopolar transition states.