4803-09-2Relevant academic research and scientific papers
Spectroscopic Characterization of 1-Naphthyl Isocyanate Anion Radical and of Tris(1-naphthyl) Isocyanurate Atropisomers
Peters, Steven J.,Kassabaum, Mark E.,Nocella, Michael K.,McDonald, Robert
, p. 6040 - 6046 (2015)
Room-temperature potassium metal reduction of 1-naphthyl isocyanate in THF results in a rapid cyclotrimerization (initiated by the 1-naphthyl isocyanate anion radical) that generates two diastereoisomers (atropisomers) of tris(1-naphthyl) isocyanurate. The formation of the syn and anti diastereoisomers was monitored by 1H and 13C NMR spectroscopy. Upon completion of the cyclotrimerization, the two diastereoisomers were isolated, and their configuration was assigned by NMR spectroscopy. Both compounds crystallize in the monoclinic C2/c space group, and single-crystal X-ray diffraction analyses confirm the structures of both isomeric forms. The results from this study prove that alkali metal reduction of isocyanates is a convenient and rapid method for generating isocyanurate compounds even when a sterically bulky substituent is attached to the NCO moiety.
Fast cyclotrimerization of a wide range of isocyanates to isocyanurates over acid/base conjugates under bulk conditions
Cheng, Ruihua,Liu, Wei,Wu, Li,Ye, Jinxing
, (2020/07/06)
An array of organic bases DMAP (4-dimethylaminopyridine), DBU (1, 8-diazabicyclo [5.4.0] undec-7-ene), TBD (1, 5, 7-triazabicyclo [4.4.0] dec-5-ene), and their base/acid conjugate organocatalyst systems were evaluated in the trimerization of various isocyanates. The performance depended greatly on the combination of the catalyst systems, and the [HTBD][OAc] (acetic acid) catalyst systems were considerably the most active in contrast to the corresponding DMAP and DBU counterparts. The [HTBD][OAc] catalyst system was capable of providing isocyanurates from the cyclotrimerization of various isocyanate substrates in excellent yields in seconds even under bulk conditions. A bifunctional catalytic mechanism over [HTBD][OAc] was proposed.
Potassium complexes containing bidentate pyrrole ligands: Synthesis, structures, and catalytic activity for the cyclotrimerization of isocyanates
Guo, Zhiqiang,Xu, Yuan,Wu, Xiaoqin,Wei, Xuehong,Xi, Chanjuan
supporting information, p. 8116 - 8121 (2019/06/19)
Bidentate pyrrolyl ligands, 2-(t-butyliminomethyl)pyrrole and 2-(t-butylaminomethyl)pyrrole, reacted with KH to give complexes [C4H3N(2-CHNtBu)K(THF)]n (1) and [C4H3N(2-CH2NHsup
An expeditious method for the selective cyclotrimerization of isocyanates initiated by TDAE
Giuglio-Tonolo, Alain G.,Spitz, Cédric,Terme, Thierry,Vanelle, Patrice
, p. 2700 - 2702 (2014/05/06)
We developed a rapid and green synthesis of various isocyanurates by cyclotrimerization of isocyanates using TDAE (tetrakis(dimethylamino)ethylene). TDAE displays excellent performance in catalytic quantities, affording the corresponding trimer of isocyanates very rapidly, under air and at room temperature in good to excellent yields.
Organocatalytic, rapid and facile cyclotrimerization of isocyanates using tetrabutylammonium phthalimide-N-oxyl and tetraethylammonium 2-(carbamoyl)benzoate under solvent-free conditions
Dekamin, Mohammad G.,Varmira, Kambiz,Farahmand, Mehdi,Sagheb-Asl, Solmaz,Karimi, Zahra
experimental part, p. 226 - 230 (2011/09/14)
Tetrabutylammonium phthalimide-N-oxyl and tetraethylammonium 2-(carbamoyl)benzoate were found to be effective and easily accessible organocatalysts for selective cylotrimerization of aryl and alkyl isocyanates under mild reaction conditions. The reaction proceeds smoothly using very low catalyst loadings of these metal-free organocatalysts (0.025 and 0.25 mol%, respectively) under solvent-free conditions at room temperature within a very short reaction time.
An electron-rich proazaphosphatrane for isocyanate trimerization to isocyanurates
Raders, Steven M.,Verkade, John G.
experimental part, p. 5308 - 5311 (2010/10/19)
(Figure presented) A facile synthesis of the new electron-rich, sterically hindered proazaphosphatrane shown above is described herein. This proazaphosphatrane catalyzes the cyclotrimerization of a wide variety of isocyanates to isocyanurates under mild c
The performance of phthalimide-N-oxyl anion
Dekamin, Mohammad G.,Moghaddam, Firouz M.,Saeidian, Hamdollah,Mallakpour, Shadpour
, p. 1591 - 1595 (2007/10/03)
Alkali metal salts of phthalimide-N-oxyl, including Li, Na, and K were prepared and applied as novel selective catalysts to promote the cyclotrimerization of aryl and alkyl isocyanates. This paper is addressing these salts as a new class of organic nucleo
Haloamidation of alkynes and related reactions using zirconacycles and isocyanates
Li, Yanzhong,Matsumura, Hiroshi,Yamanaka, Masamichi,Takahashi, Tamotsu
, p. 1393 - 1400 (2007/10/03)
Zirconacyclopentenes reacted with isocyanates to give aza- or oxazirconacycles which were conveniently coverted into the corresponding haloamidation products of alkynes after halogenation. 1,4-Bistrimethylsilyl substituted zirconacyclopentadiene afforded a low yield of iodoamidation product, whereas zirconium-alkyne complexes stabilized with phosphine gave the iodoamidation products in moderate yields. On the other hand, zirconacyclopentanes reacted with isocyanates to give trimerization products of isocyanate, isocyanurates.
Solvent-free efficient synthesis of symmetrical isocyanurates by a combination catalyst: Sodium saccharin and tetrabutylammonium iodide
Matloubi Moghaddam, Firouz,Koozehgiri, Gholam R.,Dekamin, Mohammad G.
, p. 849 - 851 (2007/10/03)
Combination of sodium saccharin and tetrabutylammonium iodide as a novel anionic catalyst system promotes selectively the trimerization of isocyanates to give symmetrical isocyanurates under solvent-free conditions. Springer-Verlag 2004.
Efficient and selective trimerization of aryl and alkyl isocyanates catalyzed by sodium p-toluenesulfinate in the presence of TBAI in a solvent-free condition
Moghaddam, Firouz Matloubi,Dekamin, Mohammad G.,Khajavi, Mohammad S.,Jalili, Seifollah
, p. 851 - 852 (2007/10/03)
Aryl and alkyl isocyanates have been efficiently converted into symmetrical trisubstituted aryl and alkyl isocyanurates, catalyzed by sodium p-toluenesulfinate on its own or in the presence of tetrabutylammonium iodide (TBAI), in a solvent-free condition.
