Hydro peroxides /NaNO2/KHSO4 mediated synthesis, kinetics and mechanistic study of nitration of aromatic compounds in aqueous acetonitrile

AbstractThe dehydrogenative aryl C-H/N-H cross-coupling is a powerful synthetic methodology to install nitrogen functionalities into aromatic compounds. Herein, we report an electrochemical oxidation induced intermolecular cross-coupling between aromatics and sulfonimides with high regioselectivity through N-radical addition pathway under external-oxidant-free and catalyst-free conditions. A wide variety of arenes, heteroarenes, alkenes and sulfonimides are applicable scaffolds in this transformation. In addition, aryl sulfonamides or amines (aniline derivatives) can be obtained through different deprotection process. The cyclic voltammetry mechanistic study indicates that the N-centered imidyl radicals are generated via proton-coupled electron transfer event jointly mediated by tetrabutylammonium acetate and anode oxidation process.

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Spectroscopic Properties of Polycyclic Aromatic Compounds: Examination of Nitromethane as a Selective Fluorescence Quenching Agent for Alternant Polycyclic Aromatic Nitrogen Hetero-Atom Derivatives

Applied Spectroscopy ◽

10.1366/0003702924125474 ◽

1992 ◽

Vol 46 (2) ◽

pp. 229-235 ◽

Cited By ~ 18

Author(s):

Sheryl A. Tucker ◽

William E. Acree ◽

Mary J. Tanga ◽

Sumio Tokita ◽

Kimihiro Hiruta ◽

...

Keyword(s):

Fluorescence Quenching ◽

Aromatic Compounds ◽

Fluorescence Emission ◽

Spectroscopic Properties ◽

Polycyclic Aromatic Compounds ◽

Solvent Mixtures ◽

Aqueous Acetonitrile ◽

Polycyclic Aromatic ◽

Emission Behavior

Nitromethane is examined as a selective fluorescence quenching agent for alternant polycyclic aromatic nitrogen hetero-atoms (PANHs). Fluorescence emission behavior is reported for 1-azapyrene, 2-azapyrene, 4-azapyrene, 4-azachrysene, 12-azabenzo[a]pyrene, phenanthro[9, 10g]isoquinoline, phenanthro[2,3h]isoquinoline, phenanthro[3,2h]-isoquinoline, 2-azabenz[a]anthracene, 1-azabenz[a]anthracene, 9-azabenz[a]anthracene, dibenzo[c,i]phenanthro[1,10,9,8anmlk]phenanthridine, diphenanthro[9,10,1def;1',10',9'hij]phthalazine, and benz[de]isoquino[1,8gh]quinoline dissolved in acetonitrile or aqueous-acetonitrile solvent mixtures at various nitromethane concentrations. Results of these measurements show that nitromethane does quench fluorescence emission of ten of the solutes studied; however, phenanthro-[2,3h]isoquinoline, 9-azabenz[a]anthracene, benz[de]isoquino[1,8gh]-quinoline, and dibenzo[c,i]phenanthro[1,10,9,8anmlk]phenanthridine are notable exceptions.

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SYNTHETIC UTILITY OF N-CHLOROSUCCINIMIDE IN THE OXIDATION OF ISATIN IN AQUEOUS ACETONITRILE MEDIUM – A KINETIC AND MECHANISTIC STUDY

International Journal of Biology Pharmacy and Allied Sciences ◽

10.31032/ijbpas/2021/10.12.5778 ◽

2021 ◽

Vol 10 (12) ◽

Keyword(s):

Mechanistic Study ◽

Aqueous Acetonitrile ◽

Synthetic Utility ◽

Acetonitrile Medium

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Mechanistic study of the rhodium-catalyzed carboxylation of simple aromatic compounds with carbon dioxide

Chemical Science ◽

10.1039/c6sc03838g ◽

2017 ◽

Vol 8 (2) ◽

pp. 1454-1462 ◽

Cited By ~ 36

Author(s):

Takuya Suga ◽

Takanobu Saitou ◽

Jun Takaya ◽

Nobuharu Iwasawa

Keyword(s):

Carbon Dioxide ◽

Aromatic Compounds ◽

Mechanistic Study

A detailed mechanistic study of the rhodium-catalyzed carboxylation of aromatic compounds was carried out to clarify the unique characteristics of this reaction.

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