78227-85-7Relevant academic research and scientific papers
Ionic Reactivity of 2-Isocyanoaryl Thioethers: Access to 2-Halo and 2-Aminobenzothia/Selenazoles
Bao, Lan,Dong, Jinhuan,Hu, Junlin,Jia, Mengying,Liu, Xiaoli,Sun, Shaoguang,Xu, Xianxiu
supporting information, (2022/02/23)
An ionic cascade insertion/cyclization reaction of thia-/selena-functionalized arylisocyanides has been successfully developed for the efficient and practical synthesis of 2-halobenzothiazole/benzoselenazole derivatives. This synthetic protocol, incorporating a halogen atom when forming the five-membered ring of benzothia/selenazoles, is different from the existing ones, where halogenation of the preformed benzothia/selenazole precursors happens. Additionally, a facile access to 2-aminobenzothiazoles is also achieved by the one-pot cascade reaction of 2-isocyanoaryl thioethers, iodine, and amines.
Sparing the Ortho-position in Nucleophilic Aromatic Substitution-Specific Displacement of the 4-SePh Group in 2,4-Bis(phenylseleno)nitrobenzene
Nicolai, Stuhr-Hansen,Goetze, Thorstein Finn,Henriksen, Lars,Solling, Theis Ivan,Langkilde, Annette,Sorensen, Henning Osholm
experimental part, p. 101 - 108 (2009/09/25)
Upon treatment of o- and p- (phenylseleno)nitrobenzenes with sodium methoxide quantitative exchange reactions took place, affording the corresponding methoxynitrobenzenes. Upon reaction between 2,4-bis(phenylseleno) nitrobenzene 2 and sodium methoxide, an unusual regiopure formation of 4-methoxy-2-(phenylseleno)nitrobenzene 3 was observed. This product remained unreactive toward an excess of sodium methoxide, thus preventing the formation of 2,4-dimethoxynitrobenzene 6. The nature of the reactants and of the intermediate Meisenheimer complexes was examined by synthetic investigations, x-ray crystallography, and DFT calculations. We found that the observed selectivity can be understood in terms of traditional resonance considerations.
THE THIOLATE ANION AS A NUCLEOPHILE PART X. REACTIONS OF SOME NITROFLUOROAROMATICS
Leblanc, Maurice E.,Peach, Michael E.,Winter, Heather M.
, p. 233 - 248 (2007/10/02)
The reactions of various nitrofluorobenzenes, C6HxFyNO2, with sodium methanethiolate have been studied in ethylene glycol/pyridine mixture as solvent.All the fluorine atoms, but not the nitrogroups, could be substituted by the methylthio group.The reactions have also been studied with the addition of a deactivating group, either methyl or amino, on the aromatic nucleus.Some of the methylthio groups in the products were oxidized to the corresponding sulfones.The new compounds isolated have been characterized and their spectra (IR, NMR and mass) examined.
