941-55-9Relevant articles and documents
Isolation of a labile homoleptic diazenium cation
Baumann, Wolfgang,Michalik, Dirk,Reiss, Fabian,Schulz, Axel,Villinger, Alexander
, p. 3250 - 3253 (2014)
Following our interest in nitrogen chemistry, we now describe the synthesis, structure, and bonding of labile disilylated diazene, its GaCl 3 adduct, and the intriguing trisilylated diazenium ion [(Me 3Si)2Ni=N-SiMe3]+, a dark blue and highly labile (Tdecomp>-30 °C) homoleptic cation of the type [R3N2]+. Although direct silylation of Me 3Si-Ni=N-SiMe3 failed, the [(Me3Si) 2Ni=N-SiMe3]+ ion was generated in a straightforward two-electron oxidation reaction from mercury(II) dihydrazide and Ag[GaCl4]. Moreover, previous structure data of Me 3Si-Ni=N-SiMe3 were revised on the basis of new data. Cold, blue, and positive: The first homoleptic diazenium cation has been formed by treating mercury(II) dihydrazide with Ag[GaCl4] at low temperature. While numerous attempts at the direct silylation of diazene failed, this alternative new two-electron oxidation of the trisilylated hydrazide ion affords blue, highly labile [(Me3Si)2Ni=N-SiMe 3]+ ions in almost quantitative yield.
Synthesis and characterization of redox active cyrhetrene-triazole click products
Day, David P.,Dann, Thomas,Blagg, Robin J.,Wildgoose, Gregory G.
, p. 29 - 34 (2014)
We report the synthesis and characterization of two new cyclopentadienyl tricarbonyl rhenium(I) (cyrhetrene) complexes modified with a 1,4-disubstituted 1,2,3-triazole moiety. The two compounds, (η5-[4-phenyltriazol-1-yl]cyclopentadienyl) trica
Synthesis and Reactivity of 5-Heterotruxenes Containing Sulfur or Nitrogen as the Heteroatom
Górski, Krzysztof,Mech-Piskorz, Justyna,Le?niewska, Barbara,Pietraszkiewicz, Oksana,Pietraszkiewicz, Marek
, p. 11553 - 11561 (2019)
This paper presents an alternative path for the synthesis of 5-thiatruxene and the synthetic approach for 5-azatruxene not known so far. A new method for 5-thiatruxene improves the overall reaction yield from 17.5 to 22.6%, diminishes the synthesis time and costs by reducing synthetic steps from 5 to 2, and simplifies the isolation of intermediate and final products. The overall reaction yield for 5-azatruxene is 32.4%. The typical reactivity of both aromatic systems is also demonstrated. Recent research results suggest the use of 5-thiatruxene as the acceptor subunit of soluble blue emitters.
Copper(I)-Catalyzed Ketenimine Formation/Aza-Claisen Rearrangement Cascade for Stereoselective Synthesis of α-Allylic Amidines
Wang, Cheng-Gang,Wu, Rui,Li, Ting-Peng,Jia, Tao,Li, Yang,Fang, Dongmei,Chen, Xiaozhen,Gao, Yuanji,Ni, Hai-Liang,Hu, Ping,Wang, Bi-Qin,Cao, Peng
, p. 3234 - 3238 (2020)
A copper-catalyzed three-component reaction of terminal alkynes, TsN3, and tertiary allylic amines is developed toward the one-pot synthesis of α-allylic amidines. The product was synthesized on gram scale under 1 mol % of catalyst loading. Transformations of products into alkenyl amine and other nitrogen-containing compounds are demonstrated without any loss of stereochemical information.
Tandem Fragmentation of Cyclopropylcarbinyl/Oxiranylcarbinyl Radicals. On the Reversibility of Oxiranylcarbinyl/Allyloxyl Radical Formation
Ziegler, Frederick,Petersen, Anders K.
, p. 2707 - 2714 (1994)
The tandem radical fragmentation of four stereoisomeric epoxy thiocarbonates 7c-10c has been investigated.In each instance a cyclopropylcarbinyl radical fragments to generate an oxiranylcarbinyl radical, which, in turn, undergoes fragmentation.The initially detected product is (Z)-allylic alcohol 23, which isomerizes to (E)-allylic alcohol 24 under acid catalysis.The reversibility of allyloxyl radical formation is considered.
Powerful Direct C-H Amidation Polymerization Affords Single-Fluorophore-Based White-Light-Emitting Polysulfonamides by Fine-Tuning Hydrogen Bonds
Choi, Tae-Lim,Hwang, Soon-Hyeok,Kim, Hongsik,Lee, Dongwhan,Ryu, Hanseul,Serdiuk, Illia E.
supporting information, p. 1778 - 1785 (2022/01/19)
The development of white-light-emitting polymers has been actively pursued because of the importance of such polymers in various applications, such as lighting sources and displays. To generate white-light, numerous research efforts have focused on synthe
Synthesis of Functionalized Silsesquioxane Nanomaterials by Rhodium-Catalyzed Carbene Insertion into Si?H Bonds
Franz, Annaliese K.,Jagannathan, Jake R.,Targos, Karina
supporting information, (2021/11/27)
We report carbene insertion into Si?H bonds of polyhedral oligomeric silsesquioxanes (POSS) for the synthesis of highly functionalized siloxane nanomaterials. Dirhodium(II) carboxylates catalyze insertion of aryl-diazoacetates as carbene precursors to afford POSS structures containing both ester and aryl groups as orthogonal functional handles for further derivatization of POSS materials. Four diverse and structurally varied silsesquioxane core scaffolds with one, three, or eight Si?H bonds were evaluated with diazo reactants to produce a total of 20 new POSS compounds. Novel diazo compounds containing a fluorinated octyl group and boron-dipyrromethene (BODIPY) chromophore demonstrate the use of highly functionalized substrates. Transformations of aryl(ester)-functionalized POSS compounds derived from this method are demonstrated, including ester hydrolysis and Suzuki–Miyaura cross-coupling.
Ambruticins: tetrahydropyran ring formation and total synthesis
Bowen, James I.,Crump, Matthew P.,Wang, Luoyi,Willis, Christine L.
supporting information, p. 6210 - 6215 (2021/07/28)
The ambruticins are a family of polyketide natural products which exhibit potent antifungal activity. Gene knockout experiments are in accord with the proposal that the tetrahydropyran ring of the ambruticins is formedviathe AmbJ catalysed epoxidation of the unsaturated 3,5-dihydroxy acid, ambruticin J, followed by regioselective cyclisation to ambruticin F. Herein, a convergent approach to the total synthesis of ambruticin J is described as well as model studies involving epoxidation and cyclisations of unsaturated hydroxy esters to give tetrahydropyrans and tetrahydrofurans. The total synthesis involves preparation of three key fragments which were unitedviaa Suzuki-Miyaura cross-coupling and Julia-Kocienski olefination to generate the required carbon framework. Global deprotection to a triol and selective oxidation of the primary alcohol gave, after hydrolysis of the lactone, ambruticin J.
Catalyst-free, scalable heterocyclic flow photocyclopropanation
Kl?pfer, Viktor,Eckl, Robert,Flo?, Johannes,Roth, Philippe M. C.,Reiser, Oliver,Barham, Joshua P.
supporting information, p. 6366 - 6372 (2021/09/10)
Industrial process development is driven by several factors, including safety, cost, robustness and environmental aspects. However, attempts to establish aryl diazo esters-which are highly valued in academic research for their reactivity as carbene precur
Catalyst-free one-pot, four-component approach for the synthesis of di- And tri-substituted: N -sulfonyl formamidines
Liu, Ai-Ran,Zhang, Lei,Li, Jiao,Wusiman, Abudureheman
, p. 15161 - 15166 (2021/05/19)
A straightforward one-pot, multicomponent approach was developed to synthesize di- and tri-substituted N-sulfonyl formamidines from sulfonyl chlorides, NaN3, ethyl propiolate, and primary/secondary amines under mild conditions without catalysts or additives. Structural analysis of the di-substituted sulfonyl formamidines indicated formation of the E-syn/anti isomeric form. Tri-substituted analogues only formed E-isomers.
