39963-93-4Relevant academic research and scientific papers
Folding-driven reversible polymerization of oligo(m-phenylene ethynylene) imines: Solvent and starter sequence studies
Zhao, Dahui,Moore, Jeffrey S.
, p. 2712 - 2720 (2003)
Bis(imino) end-functionalized oligo(m-phenylene ethynylene)s were equilibrated in a closed system under conditions that promote reversible imine metathesis. The metathesis reaction joins two oligomers and produces a small molecule byproduct. In polar solvents, equilibration gave high molecular weight polymers while equilibration in chloroform produced only low molecular weight oligomers. This polymerization is hypothesized to be driven by the free energy gained from the folding of the long polymer chains directed by the noncovalent, intramolecular aromatic stacking and solvophobic interactions. This polymerization was also conducted in a series of solvents in which m-phenylene ethynylene oligomers have previously shown varied, intermediate folding stabilities. These experiments revealed a good correlation of the product molecular weight with the stability of the m-phenylene ethynylene helix. The equilibrium state of the metathesis reaction was also demonstrated to depend on the chain length of the starter sequences. With a pair of trimeric precursors, macrocyclization instead of polymerization takes place. Consistent with the notion that the polymerization is a consequence of the intramolecular solvophobic chain association, higher degrees of polymerization followed from enhanced solvophobicity of the m-phenylene ethynylene backbone, achieved by appending a methyl substituent to half of the repeat units. The considerably longer equilibration time required by these more stabilized sequences suggests that the elongation process may involve unfolding or partial unfolding of the chain; alternatively, intermolecular association may be responsible for the slow chain growth.
A novel water-dispersible and magnetically recyclable nickel nanoparticles for the one-pot reduction-Schiff base condensation of nitroarenes in pure water
Ghamari Kargar, Pouya,Ravanjamjah, Asiye,Bagherzade, Ghodsieh
, p. 1916 - 1933 (2021/07/10)
In this work, a heterogeneous nanocatalyst called Ni-Fe3O4@Pectin~PPA ~ Piconal was first synthesized, which was investigated as a bifunctional catalyst containing nickel functional groups. On the other hand, this Ni-Fe3O4@Pectin~PPA ~ Piconal catalyst in aqueous solvents shows a very effective performance at ambient temperature for the nitroarene reduction reaction with sodium borohydride, for which NaBH4 is considered as a reducing agent. This is a novelty magnetic catalyst that was approved by various methods, including Fourier-transform infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD), Dynamic light scattering (DLS), Transmission electron microscopy (TEM), vibrating sample magnetometer (VSM), Inductively coupled plasma (ICP), Energy-dispersive X-ray spectroscopy (EDX), and Field emission scanning electron microscopy (FESEM) analyses. From the satisfactory results obtained from the reduction of nitrogen, this catalytic system is used for a one-pot protocol containing a reduction-Schiff base concentration of diverse nitroarenes. It was corroborated with the heterogeneous catalytic experiments on the one-pot tandem synthesis of imines from nitroarenes and aldehydes. Finally, the novel Ni-Fe3O4@Pectin~PPA ~ Piconal catalyst could function as a more economically desirable and environmentally amicable in the catalysis field. The favorable products are acquired in good to high performance in the attendance of Ni-Fe3O4@Pectin~PPA ~ Piconal as a bifunctional catalyst. This catalyst can be recycled up to six steps without losing a sharp drop.
Ruthenium N-Heterocyclic Carbene Complexes for Chemoselective Reduction of Imines and Reductive Amination of Aldehydes and Ketones
Kathuria, Lakshay,Samuelson, Ashoka G.
supporting information, (2020/06/17)
Chemoselective reduction of imines to secondary amines is catalyzed efficiently by tethered and untethered, half-sandwich ruthenium N-heterocyclic carbene (NHC) complexes at room temperature. The untethered Ru-NHC complexes are more efficient as catalysts for the reduction of aldimines and ketimines than the tethered complexes. Using the best untethered complex as a catalyst, electronic and steric demands on the reaction was probed using a series of imines. Chemoselectivity of the catalyst towards imine reduction was tested by performing inter and intramolecular competitive reactions in a variety of ways. The catalyst exhibits a very high TON and TOF under anaerobic conditions.
Improving C=N bond reductions with (Cyclopentadienone)iron complexes: Scope and limitations
Cettolin, Mattia,Bai, Xishan,Lübken, Dennis,Gatti, Marco,Facchini, Sofia Vailati,Piarulli, Umberto,Pignataro, Luca,Gennari, Cesare
supporting information, p. 647 - 654 (2018/10/24)
Herein, we broaden the application scope of (cyclo-pentadienone)iron complexes 1 in C=N bond reduction. The catalytic scope of pre-catalyst 1b, which is more active than the “Kn?lker complex” (1a) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre-isolated or generated in situ. The kinetics of 1b-promoted CTH of ketimine S1 were assessed, showing a pseudo-first order profile, with TOF = 6.07 h–1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.
Effects of molecular conformation on the spectroscopic properties of 4,4′-disubstituted benzylideneanilines
Fang, Zhengjun,Wu, Feng,Yi, Bing,Cao, Chenzhong,Xie, Xin
, p. 52 - 57 (2015/10/29)
The relationship between the molecular conformation and spectroscopic properties of unsymmetrical 4,4′-disubstituted benzylideneanilines, was explored by the combination of experiment and reference data. Crystal structure information and spectroscopic beh
Oxazolidine synthesis by complementary stereospecific and stereoconvergent methods
Shaghafi, Michael B.,Grote, Robin E.,Jarvo, Elizabeth R.
supporting information; experimental part, p. 5188 - 5191 (2011/12/15)
Complementary stereospecific and stereoconvergent reactions for enantioselective synthesis of 1,3-oxazolidines are reported. In the presence of a rhodium catalyst, reaction of enantioenriched butadiene monoxide with aryl imines is stereospecific (99% ee). Alternatively, the reaction of racemic butadiene monoxide, in the presence of a chiral palladium or nickel catalyst, provides an enantioselective synthesis of 1,3-oxazolidines (up to 94% ee). Synthesis of either the cis- or trans-1,3-oxazolidines is also accomplished under catalyst control.
Palladium-catalyzed, one-pot, three-component synthesis of homoallylic amines from aldehydes, anisidine, and allyl trifluoroacetate
Grote, Robin E.,Jarvo, Elizabeth R.
supporting information; experimental part, p. 485 - 488 (2009/07/18)
(Chemical Equation Presented) An allylation reaction that generates homoallylic amines using allyl trifluoroacetate as a nucleophilic allylmetal precursor is reported. A palladium complex catalyzes two transformations in one pot: formation of allylsilane
Novel oxazabicycles as a new class of photochromic colorants
Yang, Ding-Yah,Chen, You-Sheng,Kuo, Pei-Yu,Lai, Jiun-Ting,Jiang, Chang-Ming,Lai, Chin-Hung,Liao, Yong-Hong,Chou, Pi-Tai
, p. 5287 - 5290 (2008/09/17)
(Chemical Equation Presented) A new photochromic colorant with an oxazabicyclic moiety has been synthesized by an efficient method. It turns pale red upon UV irradiation and undergoes reverse reaction while being heated. This work may open an exciting new
Pot, atom and step economic (PASE) synthesis of highly functionalized piperidines: a five-component condensation
Clarke, Paul A.,Zaytzev, Andrey V.,Whitwood, Adrian C.
, p. 5209 - 5212 (2008/02/08)
The diastereoselective pot, atom and step economic (PASE) synthesis of highly functionalized piperidines has been realized. The procedure simply involves mixing methyl acetoacetate, 2 equiv of aldehyde and 2 equiv of aniline together in the presence of InCl3. In most cases the piperidine precipitates out of solution.
Synthesis and characterization of coumarin and dimedone-derived diazabicycles
Lai, Jiun-Ting,Kuo, Pei-Yu,Gau, Yung-Her,Yang, Ding-Yah
, p. 7796 - 7800 (2008/03/11)
A series of diazabicyclic derivatives were prepared in three to four steps from p-anisidine and p-nitrobenzaldehyde. The key step of the synthesis involved the acid-catalyzed coupling of 4-aminocoumarin or dimedone derivatives with amino alcohols 3 or 7 t
