85473-72-9

Upstream product

• 16932-45-9 1-bromo-2,6-dimethoxybenzene 
• 2785-97-9 (2,6-dimethoxyphenyl)lithium 
• 202211-52-7 tris(2,6-dimethoxybenzenethiolato)arsine 
• 151-10-0 1,3-Dimethoxybenzene 

Downstream Products

• 85473-78-5 tris(2,6-dimethoxyphenyl)antimony 
• 174644-99-6 C₂₄H₂₇AsO₇ 

Relevant academic research and scientific papers

Tertiary arsine ligands for the Stille coupling reaction

The Stille coupling reaction is one of the most important coupling reactions. It is well known that the triphenylarsine ligand can accelerate the reaction rate of Stille coupling. However, other arsine ligands have never been investigated for the Stille c

Carbonylative C?C Bond Activation of Electron-Poor Cyclopropanes: Rhodium-Catalyzed (3+1+2) Cycloadditions of Cyclopropylamides

Rh-catalyzed carbonylative C?C bond activation of cyclopropylamides generates configurationally stable rhodacyclopentanones that engage tethered alkenes in (3+1+2) cycloadditions. These studies provide the first examples of multicomponent cycloadditions t

Two-step synthesis of triarylmetals (As, Sb, Bi) starting from the metal oxides and 2,6-dimethoxybenzenethiol

Reported here is a new synthetic method of triarylmetals MAr3 (M = As, Sb, Bi). It is composed of two-step reactions starting from the metal oxides: (1) A reaction of the metal oxide with 2,6-dimethoxybenzenethiol ΦSH [Φ = 2,6-(MeO)2C6H3] in the presence of acid to give the thiolatometals M(SΦ)3, and (2) A reaction of M(SΦ)3 with organolithium reagent LiAr to give MAr3 (Ar = Ph, 4-MeC6H4, 4-Me2NC6H4, Φ). Since ΦSH is odorless and crystalline, most of it can be recovered after the reactions without difficulty for repeated usages. The intermediates M(SΦ)3 are also crystalline and inert against hydrolysis.

Reactions of tris(2,6-dimethoxyphenyl) arsine, tris(2,6-dimethoxyphenyl) stibine and tris(2,6-dimethoxyphenyl) bismuthine and their derivatives

Tris(2,6-dimethoxyphenyl)arsine and tris(2,6-dimethoxyphenyl)stibine (Φ3M(Φ = 2,6-(MeO)2C6H3; M = As an Sb)) reacted with common alkyl halides (RX) to give [Φ3M-R]X, while Φ3Bi was unreactive in benzene, or it decomposed in hot alcohols. The reactions of Φ3M (As,Sb) with butyl bromide in acetonitrile were much faster than that of triphenylphosphine. Treatments of Φ3M (P,As,Sb) with N-bromosuccinimide (NBS) gave [Φ3M-OH]Br, while Φ3Bi decomposed to give 1-bromo-2,6-dimethoxybenzene. [Φ3M-OH]Br are soluble in water, and the acidity decreased in the order M = P > As > Sb. Treatments of Φ3M (As,Sb) with aqueous hydrogen peroxide gave the oxides as hydrates, Φ3MO. xH2O (x = 1 for M = As and x = 3 for M = Sb), while Φ3Bi was unreactive or decomposed. Φ3PO was brominated by NBS to give Φ′3PO.H2O (Φ′ = 3-Br-2,6-(MeO)2C6H2), which did not react with perchloric acid. In contrast, Φ3MO.xH2O (P,As,Sb) reacted with the acid to form the stable hydroxyonium salts [Φ3M-OH]ClO4. [Φ3P-OH]ClO4 formed crystals of stable 1 : 1 adducts with a variety of amines. [Φ3As-OH]ClO4 formed 1 : 1 adducts when treated with excess amounts of several amines (triethylamine,diethylamine,isobutylamine and piperidine), but they were unstable to leave amines by recrystallization. [Φ3Sb-OH]ClO4 formed unstable adducts with these amines, or it did not form. [Φ3P-SH]ClO4 formed 1 : 1 adducts with several amines, or it was deprotonated to give Φ3PS. Φ3MO.xH2O (P,As) reacted with common RX (X = Br or I) to give [Φ3M-OR]X, but Φ3SbO.3H2O reacted to give [Φ3Sb-OH]X. [Φ3P-OR]X decomposed reversibly to give Φ3PO in solutions, although [Φ3M-OR]ClO4 (P,As) could be recrystallized.

TRIARYL-ARSINE, -STIBENE UND -BISMUTHINE MIT -OR, -NR2- UND -CHR-NMe2-GRUPPEN IN ORTHO-STELLUNG

Ortho-lithiated alkyl-arylethers.N,N-dialkylarylamines and substituted N,N-dimethylbenzylamines prepared according reaction (1) are reacted with the halides of arsine, antimony and bismuth forming the expected triarylarsines, triarylstibines and triarylbismuthines.By double lithiation the bis-arsine 37 is obtained.