80816-89-3Relevant academic research and scientific papers
Lewis Acid-catalysed Reactions of Aryl Cyclopropyl Ketones. Scope and Mechanism
Murphy, William S.,Wattanasian, Sompong
, p. 1029 - 1036 (2007/10/02)
The effects of aryl substituents on the stannic chloride-catalysed cyclisation of aryl cyclopropyl ketones (1) to aryl tetralones (2) are consistent with the formation of a benzyl carbocation intermediate (8) or a cyclic oxonium ion intermediate (12).The
Reactions of Aryl Cyclopropyl Ketones. A New Synthesis of Aryl Tetralones
Murphy, William S.,Wattanasin, Sompong
, p. 2920 - 2926 (2007/10/02)
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 rigig 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.
TRAPPING THE INTERMEDIATE INVOLVED IN THE INTRAMOLECULAR CYCLISATION OF CYCLOPROPYL KETONES. A CONVENIENT PREPARATION OF OPEN-CHAIN γ-HYDROXY KETONES.
Murphy, William S.,Wattanasin, Sompong
, p. 3517 - 3520 (2007/10/02)
The concerted mechanism for the stannic chloride catalysed cyclisation of aryl cyclopropyl ketones is disproved by trapping the intermediate.The reaction provides a facile route to γ-hydroxyketones.
