Kim, HS Kim, YJ Bae, JY Kim, SJ Lah, MS Chin, CS 2024-01-21T08:39:10Z 2024-01-21T08:39:10Z 2021-09-03 2003-06-09 0276-7333 https://pubs.kist.re.kr/handle/201004/138467 The reactions of KSeO2(OCH3) (1) in methanol with [Rmim]Cl (Rmim = 1-alkyl-3-methylimidazolium) at room temperature give imidazolium-based ionic liquids containing methylselenite anion, [Rmim] [SeO2(OCH3)] (2a, R = n-C4H9; 3a, R = C2H5; 4a, R = CH3) respectively. Similarly, phosphonium methylselenites, [R4P][SeO2(OCH3)] (6a, R = n-butyl; 7a, R = ethyl) were prepared by reacting 1 with tetraalkylphosphonium bromides. The methoxy groups in imidazolium and phosphonium methylselenites were easily replaced by other alkoxy groups upon interaction with various alcohols. [1,3-dimethylimidazolium] [SeO2-(OCH3)] (4a) is slowly transformed into [1,3-dimethylimidazolium](2)[Se2O5] (5a) in the absence of methanol. An X-ray study reveals that 5a is a dimeric selenium complex consisting of two 1,3-dimethylimidazolium cations and Se2O52- anion. All the ionic liquid compounds containing methylselenite anion show surprisingly high activity for the oxidative carbonylation of aniline, even at temperatures as low as 40 degreesC, to give diphenylurea in high yield. The effects of molar ratio of aniline to catalyst, temperature, and solvent have been investigated. The plausible mechanism for the carbonylation reaction of aniline based on the H-1 and C-13 NMR studies using 3a is presented. English AMER CHEMICAL SOC IONIC LIQUIDS CARBON-MONOXIDE N,N-DIPHENYLUREA SYNTHESIS AROMATIC-AMINES CYCLIC UREAS PALLADIUM ANILINE REDUCTION HYDROFORMYLATION NITROAROMATICS Imidazolium and phosphonium alkylselenites for the catalytic oxidative carbonylation of amines: Mechanistic studies Article 10.1021/om030005f 1 ORGANOMETALLICS, v.22, no.12, pp.2498 - 2504 ORGANOMETALLICS 22 12 2498 2504 scie scopus 000183363700023 2-s2.0-0038236917 Chemistry, Inorganic & Nuclear Chemistry, Organic Chemistry Article IONIC LIQUIDS CARBON-MONOXIDE N,N-DIPHENYLUREA SYNTHESIS AROMATIC-AMINES CYCLIC UREAS PALLADIUM ANILINE REDUCTION HYDROFORMYLATION NITROAROMATICS