Generation of Carbon-Carbon Double Bonds from β-Oxygenated Phenylseleno, Phenylthio, and Iodo Species. A New Use for the Chlorotrimethylsilane-Sodium Iodide Reagent

Article abstract of DOI:10.1021/jo00315a001

A variety of β-oxygenated selenides, as exemplified by phenylseleno lactones, ethers, and alcohols are converted into olefins by treatment with Me3SiCl 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 (Z)-oct-4-ene illustrates the process.