Abstract
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.
Highlights
Adamantane (Tricyclo[3.3.1.1(3,7)]decane, Ad, 0) (Scheme 1) can be oxidized to different compounds in different ways
With the volume of the oxidizing solution V(H2O2) = 1 mL and the mass of the catalyst m = 30 mg in the reaction temperature range T = 40–70 ◦C (10 ◦C–step) and reaction times t = 5, 30, and 60 min, the composition of the 0 oxidation products does not depend on t and T
The maximum value of C = 100% is reached at V(H2O2) = 0.625 mL, and the entire studied area is divided into three parts I, in this reaction (II), and III (Figure 8)
Summary
Adamantane (Tricyclo[3.3.1.1(3,7)]decane, Ad, 0) (Scheme 1) can be oxidized to different compounds in different ways. In the general Scheme 1 and further in the numbering used in this paper, the numbers 0, 1, 2, 3, 4, and 5 indicate the number of oxygen atoms in the composition of the chemical compound. 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).
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
