Addition of silyloxydienes to 2-substituted 1, 4-benzoquinones and 1, 4-naphthoquinones

MA Brimble, RJR Elliott

Index: Brimble, Margaret A.; Elliott, Richard J.R. Tetrahedron, 1997 , vol. 53, # 22 p. 7715 - 7730

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Citation Number: 40

Abstract

Addition of 1-trimethylsilyloxybuta-1, 3-diene 2 to the quinones 4, 5, 6, 17, 18, 19, 20 bearing formyl, acetyl, methoxycarbonyl or carboxamide substituents at C-2, afforded the Diels-Alder adducts 11, 12, 13, 25, 26, 27, 28 whereas addition of 2-trimethylsilyloxyfuran 3 afforded the fragmentation products 29, 30, 31, 35, 36, 37, 38. Quinones 7, 21 bearing a carboxyl group at C-2 afforded 1, 4-naphthoquinone and 9, 10-anthracenedione with 2 and no adducts ...