The Journal of Organic Chemistry

Selenium in synthesis. Conjugated vinylic ethers, esters, and halides from. alpha.-hetero-substituted selenides

N Ikota, B Ganem

Index: Ikota,N.; Ganem,B. Journal of Organic Chemistry, 1978 , vol. 43, # 8 p. 1607 - 1608

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Citation Number: 15

Abstract

(LDA, THF-HMPA,-70" C) using phenylselenenyl bromide or diphenyl diselenide afforded 4a and 4b without complication. When solutions of these arylseleno esters in ethyl acetate were treated with 30% HzOz (4-6 equiv) at 0" C for 2 h, the enol pyruvates 5a and 5b were produced in 30 and 36% yields, respectively, after column chromatography. In related experiments we had occasion to prepare two other hetero-substituted selenides. ...