Formation of cyclopropylazoarenes in the azo coupling reactions of the cyclopropanediazonium ion with active aromatic compounds

Tomilov, Yury V.; Kostyuchenko, I. V.; Shulishov, E. V.; Нефедов, О. М.

doi:10.1070/mc2002v012n03abeh001595

Cited by 13 publications

(9 citation statements)

References 8 publications

(8 reference statements)

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“…37 1,3-Dipolar cycloaddition of diazocyclopropane (1) to phenyl vinyl sulfide, 38 divinyl ether 37 and methylidenecyclopropane 4 occurs with low efficiency (the yields of dihydropyrazoles are 5%, 13% and 12%, respectively). The reaction with methylidenecyclopropane gave a mixture of two regioisomers 41a,b in the ratio * 3 : 1; in addition to dihydropyrazoles, the reaction of cyclopropylidene with methylidenecyclopropane also gave dispiro[2.0.2.1]heptane (42). As it could be expected, cyclopropyl methyl ether and allene were the main side products of decomposition of cyclopropylnitrosourea (2a).…”

Section: Cycloaddition Involving Diazocyclopropanementioning

confidence: 79%

Synthesis and properties of nitrogenous heterocycles containing a spiro-fused cyclopropane fragment

Tomilov¹,

Kostyuchenko²,

Нефедов³

2000

Russ. Chem. Rev.

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Corrosion-related defects in pure Al and AA 2037 Al alloy have been investigated by positron beam-based Doppler broadening energy spectroscopy. Defect profiles have been analyzed by measuring the S parameter as a function of incident positron energy up to 30 keV. When pure Al samples are immersed in 1M NaOH for various times, a significant increase in the S parameter near the surface is observed. This implies that the corrosion process involves the creation of defects and nanometer voids. In contrast, a significant decrease in the S parameter is observed after the corrosion of water-quenched Al alloy by the same method, which is interpreted as being a result of Cu enrichment near the metal-oxide interface layer.

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Section: Cycloaddition Involving Diazocyclopropanementioning

confidence: 79%

Synthesis and properties of nitrogenous heterocycles containing a spiro-fused cyclopropane fragment

Tomilov¹,

Kostyuchenko²,

Нефедов³

2000

Russ. Chem. Rev.

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“…The final reaction mixture contained bromide 12, azo adduct 11, CH 2 Br 2 , allene, and cyclopropane in the molar ratio 24 : 15 : 6 : 4.5 : 1 (see Schemes 3,4).…”

Section: Methodsmentioning

confidence: 99%

“…13 C NMR (CDCl 3 ), δ: 10.77 (CH 2 CH 2 ), 49.33 (CH), 55.96 (OMe), 113.66 (C(3)), 118.40 (C(5)), 119.44 (C(6)), 135.85 (C(2)), 146.46 (C(1)), 152.70 (C (4) Reactions in the tube of an NMR spectrometer (general pro cedure). A solution of compound 1 (10 mg, 0.077 mmol) in CD 2 Cl 2 (0.4 mL) and 1 phenylpyrazolidin 3 one (5) or 4 methoxyphenol (0.07 mmol) were placed in the tube.…”

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confidence: 99%

Decomposition of N-cyclopropyl-N-nitrosourea in the presence of reducing agents as a new way of generating the cyclopropyl radical

et al. 2006

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A new way of generating cyclopropyl radicals in the base catalyzed decomposition of N cyclopropyl N nitrosourea in the presence of organic reducing agents (1 phenylpyrazolidin 3 one and 4 methoxyphenol) was developed. The cyclopropyl radical generated under these conditions can not only abstract a proton from the substrate to give cyclopropane but also form C-C or C-Br bonds in reactions with aromatic substrates or polybromomethanes.

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“…The reaction of azo coupling, taking place between diazonium salts (DS) and aromatic amines, phenols, or naphthols, results in deep-colored products (azo dyes). Therefore, it is widely used for photometric analysis of organic pollutants [ 18 – 20 ]. However, due to modest selectivity and insufficient sensitivity, the azo coupling is not fully applicable on environmental samples.…”

Section: Introductionmentioning

confidence: 99%

Solid-Phase Spectrophotometric Analysis of 1-Naphthol Using Silica Functionalized with m-Diazophenylarsonic Acid

et al. 2016

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The m-aminophenylarsonic acid (m-APAA) was immobilized onto the silica gel surface with covalently grafted quaternary ammonium groups via ion exchange. The diazotization of ion-bonded m-APAA resulted in a new solid-phase spectrophotometric reagent for detection of 1-naphtol in environmental water samples. The procedure of solid-phase spectrophotometric analysis is characterized by 20 μg L−1 limit of detection (LOD) of 1-naphtol, up to 2000 concentration factor, and insensitivity to the presence of natural water components as well as to 30-fold excess of phenol, resorcinol, and catechol.

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Formation of cyclopropylazoarenes in the azo coupling reactions of the cyclopropanediazonium ion with active aromatic compounds

Cited by 13 publications

References 8 publications

Synthesis and properties of nitrogenous heterocycles containing a spiro-fused cyclopropane fragment

Synthesis and properties of nitrogenous heterocycles containing a spiro-fused cyclopropane fragment

Decomposition of N-cyclopropyl-N-nitrosourea in the presence of reducing agents as a new way of generating the cyclopropyl radical

Solid-Phase Spectrophotometric Analysis of 1-Naphthol Using Silica Functionalized with m-Diazophenylarsonic Acid

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