171898-64-9Relevant academic research and scientific papers
Copper-catalyzed Ullmann coupling under ligand- and additive-free conditions. Part 2: S-Arylation of thiols with aryl iodides
Buranaprasertsuk, Pongchart,Chang, Joyce Wei Wei,Chavasiri, Warinthorn,Chan, Philip Wai Hong
, p. 2023 - 2025 (2008)
S-Arylation of a wide variety of substituted aryl and aliphatic thiols with aryl halides catalyzed by copper iodide under mild ligand- and additive-free conditions (nBu4NBr, PhMe, NaOH, reflux, 22 h) is accomplished in good to excellent product yields (up to 96%).
1H and 13C NMR Study of Substituted Effects in 2- and 3-Substituted Diphenyl Sulphides and Sulphones and 4-Substituted 2',6'-Dimethyldiphenyl Sulphides
Perumal, Subbu,Chandrasekaran, Ramasubbu,Vijayabaskar, Veerappan,Wilson, David A.
, p. 779 - 790 (2007/10/03)
The proton and carbon NMR spectra of nine 2-substituted diphenyl sulphides (S-2-X), seven 3-substituted diphenyl sulphides (S-3-X), nine 2-substituted diphenyl sulphones (SO2-2-X), nine 3-substituted diphenyl sulphones (SO2-3-X) and nine 4-substituted-2',6'-dimethyldiphenyl sulphides (Me2-S-4-X) were obtained.Correlations of the 1H and 13C chemical shifts were made with benzene substituent-induced chemical shifts (Lynch plots) and Hammett and dual-substituent parameters and the results were compared with those of 4-substituted diphenyl sulphides (S-4-X) and sulphones (SO2-4-X).The main conclusions are as follows: (i) the transmission of the substituent effects in substituted diphenyl sulphides decreases in the order S-4-X ca.S-2-X > Me2-S-4-X > S-3-X; (ii) the inductive effects are transmitted to a larger extent than the resonance effects to the unsubstituted ring in 3-substituted diphenyl sulphides, while the reverse trend is observed in other substituted diphenyl sulphides; (iii) in 2-methoxy-, 2-chloro-, 2-bromo- and 2-nitrodiphenyl sulphides, an increase in the size of the substituent causes an upfield shift for H-6 ascribable to the repulsion between the lone pairs of electrons on the sulphur and the substituent and its influence on the conformation; (iv) the diminished transmission of substituent effects to the remote rings in 4-substituted 2',6'-dimethyldiphenyl sulphides is probably due to the orthogonal orientation of the rings; and (v) the signal due to the H-6 of 2-substituted diphenyl sulphones suffers a downfield shift with an increase in the size of the substituent, this being ascribable to the increasing steric interaction between the 2-substituent and the sulphonyl oxygen and consequent changes in the conformation. - Keywords: NMR; 1H NMR; 13C NMR; diphenyl sulphides; diphenyl sulphones; ?-polarization
