Oxidation of Adamantane with H2O2–CF3COCF3 · 1.5 H2O in the Presence of VO(acac)2

Kislitsina, K. S.; Shchadneva, N. А.; Хуснутдинов, Р. И.

doi:10.1134/s1070428018070035

Cited by 3 publications

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“…The MS of 3a was described in two papers in 1990 and 2015 as a set of m/z (rel.int., %) [57,61]. The first one reported that the MS of 3a was: 184 (5 (M +• )), 128 (8), 127 (100), 111 (31), 110 (10), 109 (10), 85 (7), 69 (8), 55 (7), 43 (36), 41 (12), 39 (9), published for the first time [57]. In the second paper, the following MS of 3a is given: 184 (10 (M +• )), 166 (6), 150 (50), 127 (100), 111 (46), 92 (28) [61].…”

Section: Comparison Of the Results Of The Authors' And Other Methods ...mentioning

confidence: 99%

“…Oxidation of 0 can be considered from two points of view: positional selectivity and oxidation depth. The largest number of works is devoted to the oxidation of 0 to a mixture of monooxygenated (1O-Ad) products with a predominance of one of the following: 1-adamantanol (1a) [6][7][8][9][10][11][12], 2-adamantanol (1b) [13], and 2-adamantanone (1c) [14] (Scheme 1). In such works, the conversion of 0 (C) may be small.…”

Section: Introductionmentioning

confidence: 99%

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One-Stage Catalytic Oxidation of Adamantane to Tri-, Tetra-, and Penta-Ols

et al. 2021

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Tertiary tetraols of adamantane (C10H16, Tricyclo[3.3.1.1(3,7)]decan) have been widely used for the synthesis of highly symmetric compounds with unique physical and chemical properties. The methods for one-stage simultaneously selective, deep, and cheap oxidation of adamantane to tetraols of different structures have not yet been developed. In this research, chemically simple, cheap, and environmentally friendly reagents are used and that is the first step in this direction. The conditions, under which the impact of a hydrogen peroxide water solution on adamantane dissolved in acetonitrile results in full conversion of adamantane and formation of a total 72% mixture of its tri-, tetra-, and penta-oxygenated products, predominantly poliols, have been found. Conversion and adamantane oxidation depth are shown to depend on the ratio of components of the water-acetonitrile solution and the method of oxidizer solution introduction when using the dimer form of 1:1 dimethylglyoxime and copper dichloride complex as a catalyst. Under the conditions of mass-spectrometry ionization by electrons (70 eV), fragmentation across three C–C bonds of the molecular ions framework of adamantane tertiary alcohols Ad(OH)n in the range n = 0–4 increases linearly with the rise of n.

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Section: Comparison Of the Results Of The Authors' And Other Methods ...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

One-Stage Catalytic Oxidation of Adamantane to Tri-, Tetra-, and Penta-Ols

et al. 2021

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A Comprehensive Review on Selective Catalytic Methods for Functionalization of Adamantane Scaffolds

Kumar,

Annie,

Solanke

et al. 2024

Asian J Org Chem

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Over the decades, conventional techniques have been reported for the direct conversion of a substantial framework of adamantyl C(sp3)‐H/Br/COOH bonds to various C‐C, C‐N, and other C‐X bonds enabled by various catalytic conditions and reagents. There are various simple and direct methods for converting adamantane tertiary and secondary C‐(Sp3)–H/X/M bonds to quaternary/ tertiary carbon–carbon bonds that have been reported in previous years, which include methods such as catalytic approaches, cross‐coupling reactions, C‐H bond functionalization, radical reactions, organometallics, and dual catalysis, etc. The selective catalytic techniques published between 2010 and 2023 are covered in this article. These adamantane derivatives are broadly studied in various fields such as medicinal chemistry applications, drug development, supramolecular chemistry, material science, catalysts/ligands and nanotechnologies.

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