Abstract

Adamantan-1-ol (1, 1-AdOH) is the most important adamantane derivative. It is used as starting compound in the synthesis of memantine and rimantadine, and 1-adamantyl ethers are efficient antioxidant additives to oils and transmission fluids, which simultaneously improve their rheological characteristics at low temperatures [1]. A known procedure for the synthesis of alcohol 1 is based on the catalytic oxidation of adamantane (2) with m-chloroperoxybenzoic acid in the presence of metal complexes. In particular, the yield of 1 in the presence of Ni, Fe, Mn, and Co complexes [2–5] ranges from 1 to 12%. Ruthenium-containing catalysts ensured preparation of adamanatan-1-ol in 66% yield [6]. However, in the latter case the reaction was accompanied by side processes leading to adamantan2-ol, adamantan-2-one, and 1-chloroadamantane. In this communication we report for the first time the oxidation of adamantane (2) with 2,3,4,5,6-pentafluoroperoxybenzoic acid (3) catalyzed by RuCl3 · 3 H2O. 2,3,4,5,6-Pentafluoroperoxybenzoic acid (3) is a stable compound whose synthesis and application were reported for the first time in [7, 8]. Peroxy acid 3 efficiently oxidizes ∆-steroids [7] and α,β-unsaturated esters [8] to the corresponding epoxy derivatives in almost quantitative yield even in the absence of a catalyst. Taking into account unusually high activity of acid 3 in reactions with olefins, we anticipated that it can be used for the selective transformation of adamantane (2) into practically important alcohol 1.

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