Spiro-fused 2, 5-cyclohexadienones from thermal 1, 3-shifts in quinol vinyl ethers. Reactions in nonbenzenoid systems and limitations of the chemistry

JS Swenton, D Bradin, BD Gates

Index: Swenton, John S.; Bradin, David; Gates, Bradley D. Journal of Organic Chemistry, 1991 , vol. 56, # 21 p. 6156 - 6163

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Citation Number: 46

Abstract

Addition of functionalized organolithium compounds to quinone monoketals furnished 4- hydroxy-2, 5-cyclohexadienone derivatives. The 4-hydroxyl group of these molecules was then transformed into a vinyl ether, and the thermal [1, 3]-shift chemistry of theae functionalbed vinyl ethers was studied. In dienone derivativea wherein a [3, 3]-aigmahpic shift was not stereoeledronically possible, theae molecules underwent thermal and ...