A potentially general regiospecific synthesis of substituted quinones from dimethyl squarate

LM Gayo, MP Winters, HW Moore

文献索引：Gayo, Leah M.; Winters, Michael P.; Moore, Harold W. Journal of Organic Chemistry, 1992 , vol. 57, # 25 p. 6896 - 6899

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被引用次数: 54

摘要

A potentially general regiospecific synthesis of benzo-and naphthoquinones is described. This method starts with dimethyl squarate (l), which is converted to the cyclobutenone ketal 3 upon sequential treatment with an organolithium reagent and then BF3 etherate or TFAA in THF/methanol. Treatment of these with a second lithium reagent followed by hydrolysis givea the cyclobutenonea 5. Addition of an alkynyl-, alkenyl-or aryllithium agent to 5 ...