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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 8
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Original Articles

The Rearrangement of 2-Carbomethoxy-2-Phenylselenocyclohexanone1

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Pages 719-726 | Received 30 Apr 1979, Published online: 05 Dec 2006
 

Abstract

In connection with a total synthetic study we prepared 2-carbomethoxy-2-phenylselenocyclohexanone (2)2 and attempted to alkylate the ketone at the 6-position. However, to our surprise, base-promoted enolization with lithium diisopropyl amide (LDA) led to some rearrangement to the lithium enolate of 2-carbomethoxy-6-phenyl-selenocyclohexanone (3).

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