Volume 27, Issue 11
Heterocyclic Compounds
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ChemInform Abstract: π-Facial Selectivity of the Singlet Oxygen (4 + 2) Cycloaddition to Chiral Naphthalene Derivatives: The Directing Effect of Carbon- Containing Substituents.

W. ADAM

W. ADAM

Inst. Org. Chem., Univ. Wuerzburg, D-97074 Wuerzburg, Germany

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M. PREIN

M. PREIN

Inst. Org. Chem., Univ. Wuerzburg, D-97074 Wuerzburg, Germany

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First published: March 12, 1996

Abstract

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ChemInform Abstract

On photooxygenation the naphthalene derivatives (I) give the corresponding endoperoxides (II) and (III) in excellent yields. The diastereoselectivity of the singlet oxygen attack is determined and the directing effect of the various substituents R is rationalized in terms of attraction or repulsion in the transition state through electronic and steric effects.

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