3189-43-3

Usage

Uses

Used in Organic Synthesis:
Tetracyanoethylene oxide is used as a reagent in organic synthesis for its ability to react with a wide variety of organic and inorganic compounds, contributing to the formation of new chemical entities.
Used in High-Energy Material Production:
It is utilized as a strong oxidizer in the production of high-energy materials, where its powerful oxidizing capabilities are harnessed to enhance the energy output of the materials.
Used in Coordination Chemistry:
Tetracyanoethylene oxide is used as a ligand in coordination chemistry due to its ability to form stable complexes with transition metal ions, which is valuable for the study and application of metal complexes in various fields.
Used in Chemical Research:
It serves as a subject of study in chemical research for understanding its reactivity, stability, and potential applications in developing new chemical processes and compounds.

InChI:InChI=1/C6N4O/c7-1-5(2-8)6(3-9,4-10)11-5

Upstream product

• 536-80-1 iodosylbenzene 
• 670-54-2 ethenetetracarbonitrile 
• 14778-29-1 1,1,2,2,-tetracyanoethane 
• 7722-84-1 dihydrogen peroxide 
• 10028-15-6 ozone 
• 14582-05-9 4,4,5,5-Tetramethyl-1,2,3-trioxolane 

Downstream Products

• 35354-69-9 2,3-diphenyl-5-trichloromethyl-oxazolidine-4,4-dicarbonitrile 
• 19770-04-8 3,4-diphenyl-3H-oxazole-2,2,5-tricarbonitrile 
• 27781-29-9 bis-p-(N,N-dimethylaminophenyl)malonitrile 
• 7039-38-5 (Methyl-phenyl-sulfonium)-dicyanmethylid 
• 59735-42-1 2-(diphenylsulfuranylidene)malonodinitrile 
• 60308-47-6 5-dicyanomethylsulfanyl-2,3-diphenyl-[1,3,4]thiadiazolium betaine 
• 60308-48-7 5-dicyanomethylsulfanyl-3-methyl-2-phenyl-[1,3,4]thiadiazolium betaine 
• 1115-12-4 carbonyl cyanide 
• 111509-99-0 2-Cyano-3-(4-methylbenzyl)-3-morpholinoacrylonitrile 
• 83096-13-3 1-phenylimidazolium-3-dicyanomethylide 
• 83096-19-9 4-phenyl-1,2,4-triazolium-1-dicyanomethylide 

Relevant academic research and scientific papers

Understanding "on-water" catalysis of organic reactions. Effects of H+ and Li+ ions in the aqueous phase and nonreacting competitor H-bond acceptors in the organic phase: On H2O versus on D2O for Huisgen cycloadditions

For a typical Huisgen cycloaddition, carried out on water, the behavior of water molecules at the oil-water interface depended on the properties of the reactants. With weakly basic reactants, a small quantity of added H+ (HClO4, 0.0001-0.01 M) present in the aqueous phase had negligible effects, but larger quantities of H+ (HClO4, 0.1-3.0 M) increased the catalytic effect and caused protons to cross the water-organic interface and affect the products. Added Li+ ions (LiClO4, 0.1-3.0 M) had no effect for on-water reactions but enhanced the rates and endo products for in-water reactions. For these cycloaddition reactions, the product endo:exo ratios, when compared to those in organic solvents, can be used to distinguish between the on-water and in-water modes. Comparisons of organic reactions on H2O and on D2O indicate that on-water catalysis ranges from weak to strong trans-phase H-bonding for reactants with basic pKa a > ca. 2 (pKa of conjugate acid). Water shows a chameleon-type response to organic molecules at hydrophobic surfaces.

Water and organic synthesis: A focus on the in-water and on-water border. Reversal of the in-water breslow hydrophobic enhancement of the normal endo -effect on crossing to on-water conditions for huisgen cycloadditions with increasingly insoluble organic liquid and solid 2π-dipolarophiles

Measurements of the endo/exo product ratios for Huisgen cycloadditions with a series of vinyl ketones, alkyl acrylates, and substituted styrenes as dipolarophiles with phthalazinium and pyridazinium dicyanomethanide 1,3-dipoles in acetonitrile and water show that as the reactions change from in-water (large hydrophobic enhancement of endo-products) to on-water, the hydrophobic enhancement of the endo-products is reduced and partially reversed (relative to acetonitrile). An expected increase of the endo-effect with increasing hydrophobic character of the dipolarophile is overcome by decreasing water solubility causing changeover to on-water conditions. On-water reactions do not show increased cycloaddition endo-effects (relative to organic solvents) as do in-water reactions.

Cu(I)-Catalyzed Highly Enantioselective [3 + 3] Cycloaddition between Two Different 1,3-Dipoles, Phthalazinium Dicyanomethanides and Iminoester-Derived Azomethine Ylides

(Chemical Equation Presented). The Cu(I)-catalyzed highly enantioselective [3 + 3] cycloaddition between two different 1,3-dipoles, phthalazinium dicyanomethanides and iminoester-derived azomethine ylides, has been achieved under mild reaction conditions, providing novel chiral heterocyclic compounds, 2,3,4,11b-tetrahydro-1H-pyrazino[2,1-a]phthalazine derivatives, in high yields with excellent diastereo- and enantioselectivies (up to 99% yield, 99% ee, >20:1 dr).

Sc(OTf)3-Catalyzed [3 + 3] Cycloaddition of Cyclopropane 1,1-Diesters with Phthalazinium Dicyanomethanides

The Sc(OTf)3-catalyzed diastereoselective [3 + 3] cycloaddition of phthalazinium dicyanomethanides with cyclopropane 1,1-diesters proceeded smoothly under mild reaction conditions, affording a variety of 3,4-dihydro-1H-pyrido[2,1-a]phthalazine derivatives in up to 99% yields with excellent diastereoselectivities.

Effect of electron-withdrawing substituents on the epoxide ring: An experimental and theoretical electron density analysis of a series of epoxide derivatives

A series of acceptor-substituted epoxide derivatives is scrutinized by means of experimental and theoretical electron-density investigations. Due to the possibility of nucleophilic ring-opening, the epoxide ring is not only a very useful functional group in organic synthesis, but acceptor-substituted epoxides are valuable building blocks for the design of protease inhibitors. Therefore, the electron-density analysis in this work focuses on two main aspects that can contribute to rational drug design: (i) the quantification of the electron-withdrawing substituent effects on the epoxide ring and (ii) the intermolecular interactions involving the epoxide ring in combination with different substituents. It can be shown that the electron-withdrawing properties of the substituents cause an elongation of the C-C bonds in the epoxide rings and the loss of electron density can be measured by an analysis of critical points, atomic charges, and the source function. The different strengths of the substituents are reflected in these properties. Covalent and electrostatic contributions to the intermolecular interactions and thus the lattice energies are depicted on different molecular surfaces.(Figure Presented)

The first, general, highly efficient method for preparing tetrasubstituted epoxides using HOF·CH3CN

Tetrasubstituted epoxides, and especially electron-depleted ones, generally are difficult to prepare. HOF·CH3CN complex, probably the best oxygen transfer agent known today, epoxidizes tetrasubstituted alkenes at 0 °C in a matter of minutes or less in excellent yields. HOF·CH3CN complex is very easy to prepare by bubbling diluted fluorine (commercial) through aqueous acetonitrile. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Dioxygen ligand transfer from platinum to molybdenum. Isolation of a highly reactive molybdenum(VI) oxoperoxo dimer

The reaction of Pt(O2)(PPh3)2 with Mo(O)2(mesityl)2 (mesityl = 2,4,6-Me3C6H2) in pyridine results in the transfer of the dioxygen ligand from platinum to molybdenum giving, in the presence of PPh4Cl, a molybdenum peroxo compound 1 in which all the organic moieties have been lost.This compound epoxidizes tetracyanoethylene at a rate estimated at 104 greater than the known oxodiperoxomolybdenum complex 2.Furthermore, 1 exhibits a high selectivity for electron-poor olefins (TCNE/cyclooctene = 103).Elemental analysis, IR and 17O NMR indicate that 1 is the tetraphenylphosphonium salt of an oxoperoxomolybdenum(VI) dimer. - Keywords: dioxygen transfer; platinum peroxo; molybdenum oxoperoxo; epoxidation

KINETIC STUDY ON PYROLYTIC ELIMINATION OF ETHYLPHENYLSULFONIUM DICYANOMETHYLIDE

Ethyl(Substituted phenyl)sulfonium dicyanomethylides (1) were prepared and pyrolyzed in sealed tubes in benzene.The rate for pyrolysis of the substrate was correlated in a good first-order kinetic equation (γ = 0.999). The rate constant was 11.4 * 10-4 s-1 at 150 deg C.Pyrolysis of (1) was found to proceed about 3 times faster than that of ethylphenylsulfonium bis(methoxycarbonyl)methylide (2).Activation parameters calculated from the Arrhenius equation were as follows: ΔH(excit.) = 128 (KJ/mol), ΔS(excit.) = 1.7 J/K/mol (150 deg C, γ = 0.999), in which the magnitude of activation enthalpy was almost the same as that of (2), while the activation entropy was considerably larger compared with that of ethyl phenyl sulfoxide (-75.1 J/K/mol).Thus, the S-Cα bond of (1) was found to be looser in the transition state.The reactivities of sulfonium ylides, sulfoxides and sulfilimines estimate the magnitude of the activation entropies of the substrates.Substituent effect on the phenyl group afforded a positive Hammet ρ-value (ρ = 0.42, γ = 0.996) vs. ?-values. From these results, it was suggested that pyrolysis of sulfonium ylides proceeds via essentially concerted intramolecular cis-elimination in which the transition state is E1-like. Key words: pyrolysis; elimination; mechanism; kinetics; sulfonium ylide.

RADICAL CARBAMOYLATION OF 1,2,3-TRIAZINIUM 2-DICYANOMETHYLIDES

The nucleophilic radical carbamoylation of 4,6-disubstituted 1,2,3-triazinium 2-dicyanomethylides occurred at their 5-positions followed by the elimination of dicyanomethylene to form 5-substituted 1,2,3-triazines.The reaction did not proceed when parent triazines were adopted as the substrates.

A COMBINED AB INITIO AND GAS ELECTRON DIFFRACTION STUDY OF THE MOLECULAR STRUCTURE OF 1,1-DICYANOCYCLOBUTANE

The molecular structure of 1,1-dicyanocyclobutane was investigated by gas electron diffraction and the results are compared with 4-21G ab initio gradient geometry refinements.In the cyclobutane ring C1-C2 > C2-C3 in contrast to structural trends generally observed for cyclobutyl systems with a single electronegative substituent.The C-CN groups are slightly non-linear, with the CN groups bent away from one another.The structural features observed can be rationalized in terms of a special electronic interaction between the geminal cyano groups, which is also suggested by the 13C NMR spectrum.