Highly selective cleavage of prenyl ethers by means of a TiCl4-n-Bu4NI mixed reagent

Article abstract of DOI:10.1016/S0040-4039(99)01717-7

Treatment of the prenyl ether of ethyl salicylate with a TiCl₄-n-Bu₄NI mixed reagent resulted in cleavage of the C-O bond to provide ethyl salicylate in quantitative yield. On the other hand, no cleavage reaction was observed when ethyl p-prenyloxybenzoate was used as a substrate. In this system, the cleavage reaction of ethers proved to be accelerated by the chelating effect of a neighboring group in the substrate.