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.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 1
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