89750-17-4Relevant articles and documents
Fe(Cp)2BF4: An efficient lewis acid catalyst for the aminolysis of epoxides
Yadav, Geeta Devi,Chauhan, Manmohan Singh,Singh, Surendra
, p. 629 - 634 (2014/03/21)
Ferrocenium tetrafluoroborate [Fe(Cp)2BF4] is an efficient Lewis acid catalyst for the aminolysis of aromatic, aliphatic, and cyclic epoxides using aniline and substituted anilines as the nucleophile to provide regioselective β-amino alcohols in 61-97% yields under solvent-free conditions at room temperature. The ring opening of cyclohexene oxide with aliphatic amines gave 2-aminocyclohexanols in 33-98% yields at 60 °C under solvent-free conditions. Georg Thieme Verlag Stuttgart New York.
The reaction of primary aromatic amines with alkylene carbonates for the selective synthesis of bis-N-(2-hydroxy)alkylanilines: The catalytic effect of phosphonium-based ionic liquids
Selva, Maurizio,Fabris, Massimo,Lucchini, Vittorio,Perosa, Alvise,Noe, Marco
experimental part, p. 5187 - 5198 (2010/12/25)
At T ≥ 140 °C, different primary aromatic amines (pX-C 6H4NH2; X = H, OCH3, CH3, Cl) react with both ethylene- and propylene-carbonates to yield a chemoselective N-alkylation process: bis-N-(2-hydroxyalkyl)anilines [pX-C 6H4N(CH2CH(R)OH)2; R = H, CH 3] are the major products and the competitive formation of carbamates is substantially ruled out. At 140 °C, under solventless conditions, the model reaction of aniline with ethylene carbonate goes to completion by simply mixing stoichiometric amounts of the reagents. However, a class of phosphonium ionic liquids (PILs) such as tetraalkylphosphonium halides and tosylates turn out to be active organocatalysts for both aniline and other primary aromatic amines. A kinetic analysis monitored by 13C NMR spectroscopy, shows that bromide exchanged PILs are the most efficient systems, able to impart a more than 8-fold acceleration to the reaction. The reactions of propylene carbonate take place at a higher temperature than those of ethylene carbonate, and only in the presence of PIL catalysts. A mechanism based on the Lewis acidity of tetraalkylphosphonium cations and the nucleophilicity of halide anions has been proposed to account for both the reaction chemoselectivity and the function of the catalysts.
The Stereochemical Investigation of 8-Membered 1,3,6-Dioxazocines via NMR
Nishiyama, Tomihiro,Iwasaki, Yoshiaki,Nishikawa, Takeshi,Miyatake, Shinji,Yamada, Fukiko
, p. 1369 - 1372 (2007/10/02)
The stereochemical properties of 2-,4-,7-, and 8-methyl substituted 5,6,7,8-tetrahydro-1,3,6-dioxazocines have been investigated by their pmr and cmr spectroscopy.On the basis of the coupling constants and γ-effects, the stereochemical structures are discussed.
