75032-28-9Relevant articles and documents
One-pot odorless thia-Michael reaction by copper ferrite nanoparticle-catalyzed reaction of elemental sulfur, aryl halides and electron-deficient alkenes
Gholinejad, Mohammad,Firouzabadi, Habib
, p. 5953 - 5959 (2015/08/06)
In this article we report a non-odorous protocol for the high yield formation of aryl-alkyl sulfides by the reaction of aryl iodides, bromides and boronic acids with elemental sulfur and electron-deficient alkenes, catalyzed by copper ferrite nanoparticles. The catalyst was easily separated using an external magnetic bar and recycled for subsequent runs, its catalytic activity being preserved.
Neighboring-Group Participation by Hydroxyl Oxygen in Nucleophilic Aromatic Substitution. Smiles Rearrangements of (ω-Hydroxyalkyl)methyl(p-nitrophenyl)sulfonium Perchlorates in Aqueous Alkali
Irie, Tadashi,Tanida, Hiroshi
, p. 4961 - 4965 (2007/10/02)
(2-Hydroxyethyl)- (1), (3-hydroxy-n-propyl)- (2), and (4-hydroxy-n-butyl)methyl(p-nitrophenyl)sulfonium perchlorates (3) were prepared.Products by Smiles rearrangements (intramolecular SNAr reactions) were obtained from 1 as β-(methylthio)ethyl p-nitrophenyl ether (9) in 37-42percent yield and from 2 as γ-(methylthio)propyl p-nitrophenyl ether (8) in quantitative yields, and none were obtained from 3.The rearrangement rates and yields were compared with an intermolecular SN2 reaction of dimethyl(p-nitrophenyl)sulfonium perchlorate (4) (displacement of the sulfonium group by a n-propoxy group) to estimate participation by the ω-hydroxyl oxygen.The rate ratios between the rearrangements (first order) and the SN2 n-propoxy attack (second order), effective molarities, were obtained as 6.02 * 103 M for 1 vs. 4 and 4.64 * 103 M for 2 vs. 4.
