A reaction of 2-iodophenol and 2-iodoanisole with 1-adamantanol in trifluoroacetic acid gives the corresponding 4-(1-adamantyl) derivatives. Similar adamantylation of 4-iodophenol and 4-iodoanisole is accompanied by migration of the iodine atom from para- to ortho-position, giving 4,6-di(1-adamantyl)-2-iodophenol and 4-(1-adamantyl)-2-iodoanisole, respectively, as the reaction products.

This study demonstrates a new rearrangement in the adamantylation reaction of 4-iodophenol and 4-iodoanisole, leading to 4,6-di(1-adamantyl)-2-iodophenol and 4-(1-adamantyl)-2

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New rearrangement in the adamantylation reaction of 4-iodophenol and 4-iodoanisole

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