Synthetic and mechanistic study of the acid-promoted aromatisation of the Diels–Alder adduct: 6,7-dimethoxy-1-(4-pyridyl)-1,4-epoxytetrahydronaphthalene-2,3-dicarboxylate

Synthetic and Mechanistic Study of the Acid-Promoted Aromatization of the Diels-Alder Adduct: 6,7-Dimethoxy-1-(4-pyridyl)-1,4epoxytetrahydronaphthalene-2,3-dicarboxylate.-The Diels-Alder reactions of the acetal (I) with dimethyl maleate (II) or fumarate (VII) give the 1,4-epoxides (III) and (IV) or (VIII) and (IX) as mixtures of exo and endo isomers. Acid-promoted aromatization is accomplished in the presence of Lewis acids such as BF 3 to give the arylnaphthalene diester (V), while Broensted acids (AcOH, TFA, MeSO 3 H) give either low or no yields or lead to formation of the by-product (IX). Kinetic experiments reveal that aromatization of the endo-epoxides is favored over that of the exo-epoxides.-(SUGAHARA,

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ChemInform Abstract: Synthetic and Mechanistic Study of the Acid‐Promoted Aromatization of the Diels—Alder Adduct: 6,7‐Dimethoxy‐1‐ (4‐pyridyl)‐1,4‐epoxytetrahydronaphthalene‐2,3‐dicarboxylate.

Sugahara¹,

Moritani²,

Kuroda³

et al. 2002

ChemInform

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Synthetic and mechanistic study of the acid-promoted aromatisation of the Diels–Alder adduct: 6,7-dimethoxy-1-(4-pyridyl)-1,4-epoxytetrahydronaphthalene-2,3-dicarboxylate

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References 18 publications

ChemInform Abstract: Synthetic and Mechanistic Study of the Acid‐Promoted Aromatization of the Diels—Alder Adduct: 6,7‐Dimethoxy‐1‐ (4‐pyridyl)‐1,4‐epoxytetrahydronaphthalene‐2,3‐dicarboxylate.

ChemInform Abstract: Synthetic and Mechanistic Study of the Acid‐Promoted Aromatization of the Diels—Alder Adduct: 6,7‐Dimethoxy‐1‐ (4‐pyridyl)‐1,4‐epoxytetrahydronaphthalene‐2,3‐dicarboxylate.

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