Volume 27, Issue 16
Preparative Organic Chemistry
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ChemInform Abstract: Acid-Catalyzed Ionic Diels-Alder Reactions in Concentrated Solutions of Lithium Perchlorate in Diethyl Ether.

P. A. GRIECO

P. A. GRIECO

Dep. Chem., Indiana Univ., Bloomington, IN 47405, USA

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J. L. COLLINS

J. L. COLLINS

Dep. Chem., Indiana Univ., Bloomington, IN 47405, USA

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S. T. HANDY

S. T. HANDY

Dep. Chem., Indiana Univ., Bloomington, IN 47405, USA

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First published: April 16, 1996

Abstract

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ChemInform Abstract

Ketals derived from α,β-unsaturated ketones undergo ionic Diels-Alder reaction with simple dienes in concentrated etheral LiClO4- solutions. Surprisingly, the ketal (XI) undergoes a facile cycloaddition under the same conditions, whereas its parent ketone does not give any cycloadduct in the etheral LiClO4-solution.

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