134-81-6Relevant articles and documents
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Matsuura,Saito
, p. 2973 (1969)
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Reductive homo-coupling of 2-aryl-2-oxazolinium salts
Shono,Kise,Nomura,Yamanami
, p. 3577 - 3580 (1993)
The reductive homo-coupling of 2-aryl-2-oxazolinium salts was achieved by reduction with Zn-CTMS, electroreduction with zinc anode, or direct electroreduction. The homo-coupled products were converted to α-diketones.
Synthesis of a new class of cationic Pd(II) complexes with 1,2,3-triazol-5-ylidene ligand and their catalytic application in the conversion of internal alkynes to 1,2-diketones
Shaik, Jeelani Basha,Ramkumar, Venkatachalam,Sankararaman, Sethuraman
, p. 1 - 8 (2018)
A new class of cationic Pd(II) complexes of the type [Pd(Tz)(Cl)(bipy)]+Cl? and [Pd (Tz)(Cl)(phen)]+Cl? (Tz = 1,4-diaryl-3-methyl-1,2,3-triazol-5-ylidene, bipy = 2,2′-bipyridine and phen = 1,10-phenanthroline) with various wing tip groups were synthesized from the corresponding 1,2,3-triazolium iodide via the corresponding chloro bridged dinuclear complexes [(Tz)(Cl)Pd(μ-Cl)2Pd(Cl)(Tz)]. The synthesized cationic complexes were screened for their catalytic activity of hydration of alkynes and found to be excellent towards the selective conversion of internal alkynes to the corresponding 1,2-diketones in good yields. A plausible mechanism was proposed for this conversion.
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Gopal,Gordon
, p. 2941,2942 (1971)
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Srinivasan,Lee
, p. 1574 (1979)
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A new hydrazone-based colorimetric chemosensor for naked-eye detection of copper ion in aqueous medium
Shi, Shao-Min,Li, Qiao,Hu, Sheng-Li
, p. 426 - 430 (2019)
A new hydrazone-based colorimetric Cu2+ chemosensor is synthesized. Its structure was confirmed by single-crystal X-ray diffraction. Its binding properties towards various metal ions are examined through absorption spectroscopy. In aqueous THF solution, the chemosensor exhibits selective recognition towards Cu2+ over other metal ions with a colour change from colourless to pink. The complex formed between the chemosensor and Cu2+ ions forms a 2:1 stoichiometry with an association constant of 2.46 × 108M?2. The analytical detection limit for Cu2+ by the naked eye is as low as 10.0 μM.
Gold-Catalyzed Intermolecular Alkyne Oxyarylation for C3 Functionalization of Benzothiophenes
Rist, Paige A.,Grainger, Richard S.,Davies, Paul W.
, p. 642 - 646 (2021)
C3-selective C-C bond formation on benzothiophenes is challenging, and few direct functionalization methods are available. A gold-catalyzed reaction of alkynes with benzothiophene S-oxides provides regioselective entry into C3-alkylated benzothiophenes with the C7-alkylated isomer as the minor product. This oxyarylation reaction works with alkyl and aryl alkynes and substituted and unsubstituted benzothiophenes. Mechanistic studies identify that sulfoxide inhibits the catalyst [DTBPAu(PhCN)]SbF6, which also degrades and forms the unreactive complex [(DTBP)2Au]SbF6.
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Michel et al.
, p. 3143 (1975)
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Wegmann,Dahn
, p. 1247,1249 (1946)
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Tinjakowa et al.
, p. 702,703; engl. Ausg. S. 719, 720 (1957)
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Albright
, p. 1977 (1974)
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Synthetic Approach to Some New Annulated 1,2,4-Triazine Skeletons with Antimicrobial and Cytotoxic Activities
Hamama, Wafaa S.,El-Bana, Ghada G.,Shaaban, Saad,Zoorob, Hanafi H.
, p. 971 - 982 (2018)
The synthesis of some triazolotriazine, tetrazolotriazine, triazinotetrazine, and triazinotetrazepino-indole by the reaction of 4-amino-6-benzyl-3-hydrazinyl-1,2,4-triazin-5(4H)-one (2) with different reagents is described. The synthesized compounds were
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Buehler
, p. 4915 (1968)
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The thermolysis and photochemistry of hybrid initiators for 'living' free radical polymerization
Skene,Connolly, Terrence J.,Scaiano
, p. 7297 - 7302 (1999)
A new initiator potentially capable of both thermal and photochemical initiation of 'living' free radical polymerization (LFRP) has been prepared. Both of these reaction pathways have been examined and identified in terms of their products. The thermal reaction is highly dependent on the reaction conditions and displays competitive radical and ionic reactivity. In the presence of a proton source, the ionic pathway is highly favored. Photochemical activation leads predominantly to Norrish type I cleavage where the photoproducts further react by α-cleavage resulting in the formation of benzaldehyde.
Metal-Free Oxidative Thioesterification of Methyl Ketones with Thiols/Disulfides for the Synthesis of α-Ketothioesters
Hu, Biao,Zhou, Pan,Zhang, Qiaohe,Wang, Yanqin,Zhao, Siyun,Lu, Lingling,Yan, Shengjiao,Yu, Fuchao
, p. 14978 - 14986 (2018)
A direct Csp3-H bond oxidative thioesterification of methyl ketones with aromatic thiols/disulfides promoted by TBAI/K2S2O8 has been developed. The reaction provides successfully a simple and efficient method for the synthesis of functionalized α-ketothioesters of aromatic thiols. This practical methodology exhibits readily available starting materials, large-scale applicability, synthetic application, and broad functional group tolerance. A possible mechanism for the transformation is proposed.
Conversion of alkynes into 1,2-diketones using HFIP as sacrificial hydrogen donor and DMSO as dihydroxylating agent
Gujjarappa, Raghuram,Vodnala, Nagaraju,Putta,Ganga Reddy, Velma,Malakar, Chandi C.
, (2020)
A metal-free and hypervalent iodine free conversion of internal alkynes into 1,2-diketo compounds has been described. The efficacy of the present protocol rely on the use of HFIP (1,1,1,3,3,3-Hexafluoro-2-propanol) as reducing agent of alkynes and DMSO as dihydroxylating agent of olefins to acquire the desired chemical transformations. The obtained 1,2-diketones were further transformed into useful derivatives.
Isoquinolinium fluorochromate: A new and efficient oxidant for organic substrates
Srinivasan,Stanley, Preethi,Balasubramanian
, p. 2057 - 2064 (1997)
Isoquinolinium fluorochromate is a versatile reagent for the effective and selective oxidation of organic substrates, in particular for alcohols, under mild conditions.
SYNTHESIS OF (Z)-STILBENDIOL DIBENZOATE BY SENSITIZED PHOTOOXYGENATION OF 2,3,5,6-TETRAPHENYL-p-DIOXIN
Lopez, Luigi
, p. 4383 - 4386 (1985)
Sensitized photooxygenation of 2,3,5,6-tetraphenyl-p-dioxin with singlet and triplet excitable sensitizers yields (Z)-stilbendiol dibenzoate together with benzil.Experimental proofs show that unconnected mechanisms could operate accounting for the 1,2-diketone and the endiol diester formation.
Laser-driven heterogeneous catalysis: Efficient amide formation catalysed by Au/SiO2 systems
Pineda, Antonio,Gomez, Leyre,Balu, Alina M.,Sebastian, Victor,Ojeda, Manuel,Arruebo, Manuel,Romero, Antonio A.,Santamaria, Jesus,Luque, Rafael
, p. 2043 - 2049 (2013)
A proof of concept of laser-assisted heterogeneously catalysed processes at room temperature using silica supported gold nanoparticles is reported. Au/SiO2 nanoparticles were laser-irradiated at 532 nm (SPR maximum absorbance) to catalyse the selected reaction, namely the production of 4-benzoylmorpholine from benzaldehyde and morpholine via amide formation, for which quantitative yields to the target amide were obtained after 3-5 h of reaction. The protocol could also be extended to a tandem oxidation/amidation process which shows the potential of the proposed approach for the promotion of liquid-phase organic reactions at room temperature.
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Berenjian et al.
, p. 4179 (1979)
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A rapid and convenient oxidation of secondary alcohols
Dip, Irene,Gethers, Christina,Rice, Tonya,Straub, Thomas S.
, p. 2720 - 2722 (2017)
A rapid (normally 20?min to 2?h) and selective oxidation of secondary alcohols to ketones can be achieved using 0.4?equivalents trichloroisocyanuric acid and 1.2?equivalents pyridine at room temperature in ethyl acetate. A likely mechanism for the reaction is proposed.
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Dittmer et al.
, p. 3676,3678 (1970)
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Stereoselective intermolecular nitroaminoxylation of terminal aromatic alkynes: Trapping alkenyl radicals by TEMPO
Yan, Hong,Rong, Guangwei,Liu, Defu,Zheng, Yang,Chen, Jie,Mao, Jincheng
, p. 6306 - 6309 (2014)
The vinyl radical is one of the most unstable organic radicals. It is demonstrated that a nitro radical attacks phenylacetylene and makes the phenyl ring deconjugated with a double bond so that the resulting vinyl radical may be stabilized by delocalization to the phenyl rings π orbital and easily trapped by TEMPO. It is noteworthy that all desired products were obtained in moderate to good yields in an (E)-configuration.
A novel application of the Dess-Martin reagent to the synthesis of an FK506 analogue and other tricarbonyl compounds
Batchelor,Gillespie,Golec,Hedgecock
, p. 167 - 170 (1993)
The use of the Dess-Martin reagent for the oxidation of β-hydroxy and β-ketoamides, esters and ketones to the corresponding tricarbonyl compounds is reported. The method is shown to be applicable to the synthesis of analogues of the immunosuppressant FK506.
Radical anions of acyclic vicinal oligoketones: An electron spin resonance study
Doerner, Thomas,Gleiter, Rolf,Neugebauer, Franz A.
, p. 2937 - 2940 (1999)
Radical anions of acyclic vicinal oligoketones with up to five CO units, 1a-d(·-) and 2a-c(·-), were generated by reduction of the parent compounds with potassium in presence of kryptofix 222 and studied by ESR measurements. The inverse correlation between g-values and the amount of spin populations on the terminal substituents prove that these radical anions are extended π-systems.
Generation of Oxyphosphonium Ions by Photoredox/Cobaloxime Catalysis for Scalable Amide and Peptide Synthesis in Batch and Continuous-Flow
Chen, Xiangyang,Houk, Kendall N.,Mo, Jia-Nan,Su, Junqi,Umanzor, Alexander,Zhang, Zheng,Zhao, Jiannan
supporting information, (2022/01/06)
Phosphine-mediated deoxygenative nucleophilic substitutions, such as the Mitsunobu reaction, are of great importance in organic synthesis. However, the conventional protocols require stoichiometric oxidants to trigger the formation of the oxyphosphonium i
Bis-Rhodamines Bridged with a Diazoketone Linker: Synthesis, Structure, and Photolysis
Belov, Vladimir N.,Bossi, Mariano L.,Hell, Stefan W.,Shojaei, Heydar
, p. 56 - 65 (2022/01/03)
Two fluorophores bound with a short photoreactive bridge are fascinating structures and remained unexplored. To investigate the synthesis and photolysis of such dyes, we linked two rhodamine dyes via a diazoketone bridge (?COCN2?) attached to p
Oxidation of: O -dioxime by (diacetoxyiodo)benzene: Green and mild access to furoxans
He, Chunlin,Pang, Siping,Zhang, Qi,Zhang, Xun,Zhao, Cheng
supporting information, p. 1489 - 1493 (2022/01/31)
Furoxan has been widely used in the field of high energy density materials because of its excellent properties such as high density, high standard enthalpy of formation and high nitrogen content. However, its existing synthesis methods are still restricted by the problems of difficult substrate preparation and manual handling of hazardous reagents. Herein, we disclosed a mild oxidation strategy to efficiently obtain furoxan derivatives starting from readily available o-dioxime substrates. This reaction features high functional group tolerance and easy scale-up, and has excellent regioselectivity for specific nonsymmetric o-dioximes. This method greatly reduces the safety risk and simplifies the operation process, and means that diversified furoxan derivatives can be easily accessed, thus paving the way for the wide application of furoxan derivatives. This journal is
