Fragmentation reaction of 1,3,5,7-tetrabromoadamantane

Моисеев, И. К.; Belyaev, P. G.; Тартаковский, В. А.

doi:10.1007/bf00854184

Cited by 1 publication

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“…Usually, 3a and 4a are synthesized as a precursor to obtaining derivatives of 3a(OR) and 4a(OR), respectively, where R is represented by many classes of compounds [38][39][40][41][42][43][44][45][46][47][48][49][50][51][52][53].…”

Section: Introductionmentioning

confidence: 99%

“…Compounds 4a(OR) by themselves and in copolymerization with other components are capable of producing stellate, reticular, and skeletal spatial structures that have numerous chemical and physical properties useful for technical applications [40][41][42][43][44][45][46][47][48][49][50][51][52][53].…”

Section: Introductionmentioning

confidence: 99%

“…For the synthesis of 3a and 4a, the two-stage scheme was most used: (I) catalytic bromination of 0 to 1,3,5-tri-and 1,3,5,7-tetra-bromadamantane (3a(Br) and 4a(Br), respectively), (II) substitution of all Br atoms for alcohol groups (Scheme 1) [40][41][42][43][44][45][46][47][48][49][50][51][52][53].…”

Section: Introductionmentioning

confidence: 99%

“…It was shown that at stage (II), along with 4a, a product of its dehydration was formed with the opening of the frame-1,5-dihydroxy-7-methylene-bicyclo [3.3.1]nona-3-one (3c) (Scheme 1), which can be separated from 4a by dissolving in ethanol and using 50% H 2 SO 4 converted into an additional amount of the target product 4a [42].…”

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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