Tetrahedron letters

Highly selective cleavage of prenyl ethers by means of a TiCl 4-n-Bu 4 NI mixed reagent

T Tsuritani, H Shinokubo, K Oshima

Index: Tsuritani, Takayuki; Shinokubo, Hiroshi; Oshima, Koichiro Tetrahedron Letters, 1999 , vol. 40, # 46 p. 8121 - 8124

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Citation Number: 25

Abstract

Treatment of the prenyl ether of 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.