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

✍ Scribed by Takayuki Tsuritani; Hiroshi Shinokubo; Koichiro Oshima

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 199 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01717-7

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✦ Synopsis

Treatment of the prenyl ether of ethyl salicylate with a TiCI4-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.

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