Issue 0, 1971

The Diels–Alder reactions of o-benzoquinones with acyclic dienes

Abstract

Diels–Alder reactions of acyclic dienes with o-benzoquinone and mono-, di-, and tri-substituted o-benzoquinones are reported. In these reactions the quinone always acts as a dienophile, with addition to the more electron-deficient olefinic linkage occurring preferentially. The adducts which are capable of aromatisation are labile, and in some cases only the aromatised adduct is isolated. These aromatised adducts, being 1,4-dihydronaphthalenes, are thermally unstable and readily lose hydrogen to give the corresponding naphthalene derivatives.

Article information

Article type
Paper

J. Chem. Soc. C, 1971, 1414-1422

The Diels–Alder reactions of o-benzoquinones with acyclic dienes

M. F. Ansell, A. J. Bignold, A. F. Gosden, V. J. Leslie and R. A. Murray, J. Chem. Soc. C, 1971, 1414 DOI: 10.1039/J39710001414

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