One-step synthesis of N-sulfonylazepines from sulfonylamides and benzene in the presence of XeF2

Kovalenko, S. V.; Brel, V. K.; Зефиров, Н. С.; Stang, Peter J.

doi:10.1070/mc1998v008n02abeh000849

Cited by 7 publications

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“…301 The reaction of XeF 2 with tetrabutylammonium salts of arenesulf-amides 156a ± c in benzene yielded N-sulfoazepines 157a ± c presumably formed as a result of generation and subsequent incorporation of nitrene into the benzene ring. 302,303 The yields of the azepines 157a ± c increase as the temperature increases. The reaction of uracil with XeF 2 in hydrofluoric acid or anhydrous hydrogen fluoride results in 5-fluorouracil (158) in small yield.…”

Section: Reactions Of Xenon Difluoride With Nitrogencontaining Compoundsmentioning

confidence: 99%

Chemistry of xenon derivatives. Synthesis and chemical properties

Brel¹,

Pirkuliev²,

Зефиров³

2001

Russ. Chem. Rev.

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The critical relaxation of the four-state Potts model on L x L lattices with L 5 64 is studied by the Monte Carlo method. The decay of the magnetisation from a nonequilibrium initial state exhibits a crossover from a power-law relaxation for I<< r ' ( L ) to an exponential one for r > > f ' ( L ) ,where t ' ( L ) is some crossover time. This crossover is discussed within the context of dynamic finite-size scaling theory. As a result, the dynamic critical exponent is estimated to be Z = 2.94 * 0.29.

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Section: Reactions Of Xenon Difluoride With Nitrogencontaining Compoundsmentioning

confidence: 99%

Chemistry of xenon derivatives. Synthesis and chemical properties

Brel¹,

Pirkuliev²,

Зефиров³

2001

Russ. Chem. Rev.

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“…Aromatic fluorination reactions have merited special attention because of useful application in materials science, the chemical industry, and medicine. − Fluorinated substitution has been carried out by the Balz-Schiemann reaction using HBF 4 with HNO 3 , which requires an amino group. , Direct substitution of the fluorine group on the benzene ring is also known by electrochemical fluorination and the use of XeF 2 ; however, their synthetic utility has been limited because of low yield and poor selectivity. − In particular, it has been difficult to perform selective monofluorination of aromatic compounds. The best oxidant is obviously dioxygen from the standpoint of green chemistry. − …”

Section: Introductionmentioning

confidence: 99%

Photocatalytic Monofluorination of Benzene by Fluoride via Photoinduced Electron Transfer with 3-Cyano-1-methylquinolinium

2013

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The photocatalytic fluorination of benzene occurs under photoirradiation of an oxygen-saturated acetonitrile (MeCN) of the 3-cyano-1-methylquinolinium ion (QuCN(+)) containing benzene and tetraethylammonium fluoride tetrahydrofluoride (TEAF·4HF) with a xenon lamp (500 W) attached to a colored-glass filter (λ < 290 nm) to yield fluorobenzene and hydrogen peroxide. The quantum yield of formation of fluorobenzene was 6%. Nanosecond laser flash photolysis measurements were performed to elucidate the mechanistic details for photocatalytic fluorination. Transient absorption spectra taken after the nanosecond laser excitation at 355 nm of a degassed MeCN solution of QuCN(+) and benzene exhibited absorption bands due to QuCN(•) (λmax = 500 nm) and the benzene dimer radical cation (λmax = 900 nm), which were generated by photoinduced electron transfer from benzene to the singlet excited state of QuCN(+). The decay rate of the transient absorption band due to the benzene dimer radical cation was accelerated by the addition of TEAF·4HF. The observed rate constant increased with increasing concentration of TEAF·4HF. The rate constant of the electrophilic addition of fluoride to the benzene radical cation was determined to be 9.4 × 10(9) M(-1) s(-1). Thus, the photocatalytic reaction is initiated by intermolecular photoinduced electron transfer from benzene to the single excited state of QuCN(+). The benzene radical cation formed by photoinduced electron transfer reacts with the fluoride anion to yield the F-adducted radical. However, QuCN(•) can reduce O2 to O2(•-), and this is followed by the protonation of O2(•-) to afford HO2(•). The hydrogen abstraction of HO2(•) from the F-adduct radical affords fluorobenzene and H2O2 as the final products.

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ChemInform Abstract: One‐Step Synthesis of N‐Sulfonylazepines from Sulfonylamides and Benzene in the Presence of XeF₂.

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One-step synthesis of N-sulfonylazepines from sulfonylamides and benzene in the presence of XeF2

Cited by 7 publications

References 12 publications

Chemistry of xenon derivatives. Synthesis and chemical properties

Chemistry of xenon derivatives. Synthesis and chemical properties

Photocatalytic Monofluorination of Benzene by Fluoride via Photoinduced Electron Transfer with 3-Cyano-1-methylquinolinium

ChemInform Abstract: One‐Step Synthesis of N‐Sulfonylazepines from Sulfonylamides and Benzene in the Presence of XeF₂.

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One-step synthesis of N-sulfonylazepines from sulfonylamides and benzene in the presence of XeF2

Cited by 7 publications

References 12 publications

Chemistry of xenon derivatives. Synthesis and chemical properties

Chemistry of xenon derivatives. Synthesis and chemical properties

Photocatalytic Monofluorination of Benzene by Fluoride via Photoinduced Electron Transfer with 3-Cyano-1-methylquinolinium

ChemInform Abstract: One‐Step Synthesis of N‐Sulfonylazepines from Sulfonylamides and Benzene in the Presence of XeF2.

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ChemInform Abstract: One‐Step Synthesis of N‐Sulfonylazepines from Sulfonylamides and Benzene in the Presence of XeF₂.