10424-68-7Relevant academic research and scientific papers
Palladium-catalyzed one-step synthesis of symmetrical diaryl sulfones from aryl halides and a sulfur dioxide surrogate
Tanaka, Hiromichi,Konishi, Hideyuki,Manabe, Kei
supporting information, p. 760 - 763 (2019/08/02)
A convenient method for the one-step synthesis of symmetrical diaryl sulfones from aryl halides has been developed. A keystone of the method is the use of K2S2O5, which can be easily and safely handled, as a sulfur dioxide surrogate. The palladium catalyst bearing P(t-Bu)3 as a ligand enables formation of the desired sulfones without significant formation of byproducts.
Syntheses of new unsymmetrical and symmetrical diaryl-sulphides and diarylsulphones containing thiazolinyl and thiazolidinonyl moieties using 4,4′-diacetyldiphenylsulphide
Abbady,Abdel-Hafez,Kandeel,Abdel-Monem
, p. 622 - 641 (2007/10/03)
Condensation of 4,4′-diacetyldiphenyl sulphide (2) with variable amounts of thiosemicarbazide (3) in refluxing ethanol and in the presence of catalytic amounts of dry piperidine afforded only 4-acetylthiosemicarbazone- 4′-acetyldiphenyl sulphide (5). Condensation of 2 with excess semicarbazide hydrochloride (4) in the presence of fused sodium acetate and/or piperidine yielded 4,4′-diacetylsemicarbazone diphenyl sulphide (6), whereas use of equimolar amounts of 2 and 4 afforded 4-acetyl-semicarbazone- 4′-acetyldiphenyl sulphide (7). 4-Acetylsemicarbazone-4′- acetylthiosemicarbazone diphenyl sulphide (8) was also obtained via two different routes. The effect of tautomeric structure 5d is discussed. 4-(4″-phenyl-Δ3-thiazoline-2″-acetylazino) -4′-acetyldiphenyl sulphide (9), 4-(5″-carboxyethyl-4″- thiazolidinone-2″-acetylazino)-4′-acetyldiphenyl sulphide (10), 4-(4″-thiazolidinone-2′-acetylazino)-4′-acetyldiphenyl sulphide (11) and 4-(4″-methyl-Δ3-thiazoline-2″- acetylazino)-4′-acetyldiphenyl sulphide (12) were prepared by interaction of 5 with phenacylbromide, bromodiethylmalonate, chloro ethylacetate and chloroacetone, respectively. Sulphides 9-12 were easily condensed with 3 to afford the corresponding 4-(heterocyclic moiety-2″-acetylazino)-4′- acetylthiosemicarbazone diphenyl sulphides 23-26. Oxidation of the prepared sulphides 5-7, 9-12, 23 and 25-26 using H2O2/glacial AcOH mixtures yielded only 4,4′-diacetyldiphenyl sulphone (13) as the main product in every case, besides 3 and 4 in certain cases. Unsymmetrical and symmetrical sulphones 14-22 were obtained starting from 13. The structures of the synthesized compounds are based on IR, 1H-NMR, 13C-NMR and mass spectral data. A theoretical study on some of the prepared compounds using molecular modeling was carried out.
The 'Inverse Electron-demand' Diels-Ader Reaction in Polymer Synthesis. Part 1. A Convenient Synthetic Route to Diethynyl Aromatic Compounds
Royles, Brodyck J. L.,Smith, David M.
, p. 355 - 358 (2007/10/02)
The simple procedure whereby acetophenone derivatives are converted, by reaction with phosphoryl chloride and N,N-dimethylformamide, into β-chlorocinnamaldehydes, and thence, by base-induced elimination, into ethynylarenes, has been extended to diketones of the type MeCOC6H4COMe (m- and p-) and (p-MeCOC6H4)2X (X = O, S, SO2, CH2, CO, or a single bond): the corresponding diethynyl compounds are obtained by this route in acceptable yield. 1,3,5-Triacetylbenzene is similarly converted into 1,3,5-triethynylbenzene.
