A useful synthon approach to bicyclic enols: acid-catalyzed and base-catalyzed rearrangements of Diels-Alder adducts of 2-methoxy-5-methyl-1, 4-benzoquinone

…, K Ueyama, K Kanematsu

文献索引：Hayakawa, Kenji; Ueyama, Kaoru; Kanematsu, Ken Journal of Organic Chemistry, 1985 , vol. 50, # 11 p. 1963 - 1969

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被引用次数: 8

摘要

Acid-and base-catalyzed reactions of Diels-Alder adducts of the title compound 1 have been investigated. Bicyclic adducts 6, 9, and 11 isomerized to the corresponding enols 8, 10, and 13 on treatment with base followed by rapid acidification. However, thermal reactions of 1 with sorbic acid esters afforded the enol products 3 directly. Similar base treatment of tricyclic adducts 15 and 17 resulted in ether cleavage to a-keto enols 16 and 18. The ...