Tetrahedron

Rearrangements in the adamantane series: Hydride shifts of the 2-(1-adamantyl)-2-propyl cation

DJ Raber, RC Fort, E Wiskott, CW Woodworth…

文献索引：Raber,D.J. et al. Tetrahedron, 1971 , vol. 27, p. 3 - 18

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被引用次数: 9

摘要

When subjected to ordinary Koch-Haaf carboxylation conditions the tertiary alcohol, 2-(1- adamantyl)-2-propanol (4) yields only the rearranged carboxylic acid, 3-isopropyl-1- adamantane carboxylic acid (5). Mechanistic evidence is presented which indicates that the rearrangement proceeds via intermolecular hydride shifts. A variety of synthetic approaches to the unrearranged 2-(1-adamantyl)-2-methylpropionic acid (1) are described, and the ...