Spiro-fused 2, 5-cyclohexadienones from the thermal 1, 3-alkyl migrations of quinol vinyl ethers. A strategy for conversion of a carbonyl carbon to a quaternary carbon

S Wang, GW Morrow, JS Swenton

Index: Wang, Shaopeng; Morrow, Gary W.; Swenton, John S. Journal of Organic Chemistry, 1989 , vol. 54, # 22 p. 5364 - 5371

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Citation Number: 21

Abstract

Reaction of p-benzoquinone monoketals with 2-lithio derivatives of acetophenone and propiophenone dimethyl ketals results in organolithium addition to the carbonyl group of the quinone monoketal to afford the ketals of 4-aryl-4-hydroxy-2, 5-cyclohexadienones. Reaction of these products with aqueous acid results in hydrolysis of the 2, 5- cyclohexadienone ketal and intramolecular mixed ketal formation between the 4-hydroxyl ...