Issue 0, 1981

Reactions of aryl cyclopropyl ketones. A new synthesis of aryl tetralones

Abstract

Aryl cyclopropyl ketones (2) cyclise to 1-tetralones (3) in the presence of a variety of acid catalysts under mild conditions. Open-chain carbinols (4) are also formed. The ratio of (3) to (4) is dependent on the aryl ring substituents. A cationic mechanism is proposed. Cyclopropyl ketones (1) do not react. Stereoelectronic factors involved in the reactivity of the rigid cyclopropyl ketone (12) are discussed. The reactions of selected phenolic cyclopropyl ketones have been investigated as anionic counterparts to the acid-catalysed reactions. No reaction is observed.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 2920-2926

Reactions of aryl cyclopropyl ketones. A new synthesis of aryl tetralones

W. S. Murphy and S. Wattanasin, J. Chem. Soc., Perkin Trans. 1, 1981, 2920 DOI: 10.1039/P19810002920

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