Vinyl 1-adamantyl ether

The sensitivity of the Claisen rearrangement to remote substituent effects has been examined using 2-adamantyl vinyl ethers and allyl 2-adamantylidene ethers a-EWG substituents favor formation of the iyn-isomer. 

Studer reported the arylation of n-butyl vinyl ether with 4-chlorotoluene using palladium diacetate or palladium dichloride with HPAd2 (Ad = adamantyl) as a ligand (Scheme 4.67) [219]. The reaction afforded a/p selectivity of 26 74. 

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