Vinyl selenides and selenoxides: preparation, conversion to lithium reagents, Diels-Alder reactivity, and some comparisons with sulfur analogs

HJ Reich, WW Willis Jr, PD Clark

Index: Reich, Hans J.; Willis, William W.; Clark, Peter D. Journal of Organic Chemistry, 1981 , vol. 46, # 13 p. 2775 - 2784

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Citation Number: 44

Abstract

A variety of aryl vinyl selenides are prepared by reaction of vinyl Grignard reagents with aryl selenenyl bromides or by reductive elimination of the adducts of [bis (arylseleno) methyl] lithiums with carbonyl compounds. Deprotonation of phenyl vinyl selenide is achieved with LDA at-78 OC in THF. Vinyl selenides with j3-alkyl groups require LiTMP and warmer temperatures (-50" C) for complete deprotonation. Allylic lithium reagents were obtained ...