ChemInform Abstract: Synthesis of 3-(Alkylaryl)-1-adamantanols.
Abstract
The l-aryladamantanes (I) are transformed in the presence of the tertiary alcohols or halides (II) and LiClO4 to the title compounds (III).
ChemInform Abstract
The l-aryladamantanes (I) are transformed in the presence of the tertiary alcohols or halides (II) and LiClO4 to the title compounds (III). The yields obtained depend on several conditions. The Optimum conditions are found to be a molar ratio of (I):(II):TFA:LiClO4 = l :l.34- l.54:2l -29:0. 15 and CH2Cl2 as the solvent. The formation of (III) is believed to proceed via hydride abstraction from the adamantanes (I) by tertiary carbocations, the latter being developed from the tertiary alkyl compounds (II). The analogous reaction of 1-phenyladamantane (IV) affords as the main product the hydrocarbon (V), whose formation is believed to proceed at the two reactive centres of (IV), i.e. the p-position of the phenyl group and a tertiary carbon atom of the adamantane moiety. The adamantanol (IIIb) is probably an intermediate.
