The Journal of Organic Chemistry

Addition of organolithium reagents to quinone silyl methyl monoketals. A useful expedient in the synthesis of p-quinols having acid-sensitive groups

AJ Stern, JS Swenton

Index: Stern, Alan J.; Swenton, John S. Journal of Organic Chemistry, 1988 ,  vol. 53,  # 11  p. 2465 - 2468

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Citation Number: 16

Abstract

Organometallic additions to quinone monoketals1t2 followed by acid hydrolysis provide an excellent route to p-quinols; however, reduction of the quinone monoketal by the organometallic reagent or rearrangement during the ketal hydrolysis serve as limitations on the method. For certain systems, the acidic conditions required for ketal hydrolysis result in fragmentation or rearrangement reactions to the virtual exclusion of p-quinol formation. ...