Generation of carbon-carbon double bonds from. beta.-oxygenated phenylseleno, phenylthio, and iodo species. A new use for the chlorotrimethylsilane-sodium iodide …

DLJ Clive, VN Kale

Index: Clive, Derrick L.J.; Kale, Vilas N. Journal of Organic Chemistry, 1981 , vol. 46, # 2 p. 231 - 234

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Citation Number: 20

Abstract

A variety of 0-oxygenated selenides, as exemplified by phenylseleno lactones, ethers, and alcohols are converted into olefins by treatment with MeaSiCl and NaI in MeCN; the reaction is stereospecific and can be extended to iodo and thio species. The conversion of 1, 3, and 4 into 2-cyclopentene-1-acetic acid, of 5 into 2-(2-cyclopenten-1-yl) ethanol, and of 9 into (fl- oct-4-ene illustrates the process.