- Novel [2.2]paracyclophane derivatives via charge-transfer complexation
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The transannular electronic interactions in [2.2]paracyclophanes affect the selectivity of the tricyanovinylation reaction with tetracyanoethylene (TCNE). In addition to the normal N-tricyanovinyl product, 4-amino[2.2]paracyclophane reacts with TCNE to give oxaziridine derivatives. In the case of reaction with 4-N-methylamino[2.2]paracyclophane, the unusual N-tricyanovinylated product as well as 4-(N-carbonitrile-N-methyl)amino[2.2]paracyclophane was isolated. The reaction of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) with 4-amino[2.2]paracyclophane results in formation of 2-cyano-3-(4-[2.2]paracyclophanyl)amino-5,6-dichloro-1,4-benzoquinone.
- Aly,Hassan,Mourad
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- New reaction of ethenetetracarbonitrile with N-arylisoindolines
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N-Arylisoindolines 1a-i react with ethenetetracarbonitrile 2 in aerated benzene by formation of [3-(2-aryl-3-dicyanomethylene-2,3-dihydro-1H-isoindol-1-ylidene)-2-aryl-2, 3-dihydro-1H-isoindol-1-ylidene]propanedinitriles 8a-i (20-36%), N-aryl-3-dicyanomethylene-isoindol-2-ones 9a-i (15-21%) and N-arylphthalimides 10a-i (4-9%) as well as 1,1,2,2-tetracyanoethane 11 (35-55%). The structure of 8d has been unambiguously confirmed by a single crystal X-ray structure analysis. A rationale for the formation of products 8-11 is presented.
- D?pp, Dietrich,Hassan, Alaa A.,Mourad, Aboul-Fetouh E.,Nour El-Din, Ahmed M.,Angermund, Klaus,Krüger, Carl,Lehmann, Christian W.,Rust, J?rg
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- The interaction of 1,1,2-tricarbamoyl-2-cyanoethane with alkyl vinyl ketones - A new approach to [3.3.3]propellanes
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Single-stage synthesis of 3,7-diacyl-2,6-diamino-9,11-dioxo-10- aza[3,3,3]propella-2,6-dienes from 1,1,2-tricarbamoyl-2-cyanoethane and alkyl vinyl ketones, is reported.
- Lyshchikov, Anatoly N.,Sheverdov, Vladimir P.,Pavlov, Valeri V.,Nasakin, Oleg E.,Khruslalev, Viktor N.
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- A three-valued photoelectrochemical logic device realising accept anything and consensus operations
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A new application of a hybrid material exhibiting the photoelectrochemical photocurrent switching (peps) effect in a three-valued logic device is reported. In contrast to other similar peps-based systems, the one described here is capable of performing basic ternary logic operations: gullibility and consensus. This journal is
- Warzecha,Oszajca,Pilarczyk,Szacilowski
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- Reactions of substituted carbohydrazides with electron-poor olefins
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Substituted carbohydrazides 1a-e reacted with ethenetetracarbonitrile (2) in dimethylformamide with formation of diacylhydrazines 4a-e and 5-amino-1-substiuted pyrazole-3,3,4-tricarbonitriles 5a-e. On the other hand, 1a-c reacted with diethyl (E)-2,3-dicy
- Hassan, Alaa A.,Ibrahim, Yusria R.,Shawky, Ahmed M.
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experimental part
p. 998 - 1004
(2009/03/11)
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- Chemical reactivity of 3-hydrazino-5,6-diphenyl-1,2,4-triazine towards π-acceptors activated carbonitriles
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Behaviour of 3-hydrazino-5,6-diphenyl-1,2,4-triazine 1 as electron donor towards different electron acceptors activated carbonitriles has been investigated and a novel fused heterocyclic system and 2,3-disubstituted 1,2,4-triazines have been obtained. Compound 1 reacts with 1,2-dicyanobenzene as π-acceptor in DMF to form benzencarboximidamide 16, while reaction of 1 with a-bromomalononitrile 17 in boiling DMF affords compound 18. On the other hand, compound 1 reacts with tetracyanoethane 23 in DMF to yield compound 24. The route of reaction in DMF indicates that charge-transfer complexation is the key intermediate to obtain new heterocyclic systems. Structures of the products are established by MS, IR, UV-Vis, CHN and 1H NMR spectral data.
- Abdel-Rahman,Abdel-Monem
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p. 838 - 846
(2008/09/18)
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- EVIDENCE FOR A SINGLE ELECTRON TRANSFER ACTIVATION IN THE HYDRIDE TRANSFER FROM AN NADH MODEL COMPOUND TO TETRACYANOETHYLENE
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New evidence for a stepwise mechanism which requires a single electron transfer activation in the hydride transfer from an NADH model compound, 1-benzyl-1,4-dihydronicotinamide (BNAH), to tetracyanoethylene (TCNE) has been presented based on the effects of pyridine on the stoichiometry of the overall reaction, the rate constant, and the kinetic isotope effect.
- Fukuzimi, Shunichi,Kondo, Yuji,Tanaka, Toshio
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p. 751 - 754
(2007/10/02)
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- REACTION OF sym-TETRACYANOETHANE WITH THE HYDRIDES OF ELEMENTS OF SUBGROUPS VI AND VIIA
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sym-Tetracyanoethane (I) forms 1:1 and 1:2 adducts with the hydrides of elements from subgroups VI and VIIA.In some cases these adducts are converted into heterocyclic compounds.
- Nasakin, O. E.,Alekseev, V. V.,Promonenkov, V. K.,Abramov, I. A.,Bulai, A. Kh.
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p. 1747 - 1749
(2007/10/02)
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- Cycloaddition Reaction of Some Representative 1-Cyclopropyl-1,3-butadienes with Tetracyanoethylene and Reaction of the Resultant Vinylcyclobutanes. An Easy Vinylcyclobutane-Cyclohexene Rearrangement
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In the reaction with TCNE, (Z)-1-cyclopropyl-1,3-butadiene (1b) as well as several 1,1-disubstituted 1,3-butadienes (1c-f) yielded vinylcyclobutane 2 as the major product particularly in a polar solvent, whereas the E isomer 1a gave the cyclohexene 3 exclusively.The resultant vinylcyclobutanes, except for 2f, isomerized easily to 3.The most reactive of all was 2c while 2b was the least reactive.The isomerization of 2c in acetonitrile in the presence of 1a yielded virtually no cross product 3a, supporting the intramolecular nature of the transformation.Since the intermediate was trapped by p-toluenethiol, the rearrangement will most probably be stepwise.The solvent effects and the substituent effects on the rate of the reaction indicate that the ionic mechanism is operating.In contrast, 2f did not rearrange at all, but, especially at elevated temperatures, it split into the two fragments, i.e., methylenemalononitrile and 4f.The lack of effect of solvent polarity on the rate suggests that the fragmentation would be a diradical stepwise process.In the reaction of other vinylcyclobutanes, also, the fragmentation became appreciable at elevated temperatures in solvents of low polarity.The extent of the fragmentation depends upon the substituent(s) at the terminal carbon of the vinyl group.
- Kataoka, Fumio,Shimizu, Nobujiro,Nishida, Shinya
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p. 711 - 716
(2007/10/02)
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- Hydrogen transfer Reactions, Part 4. Mechanism in the Stereoselective Hydrogen Transfer from 1,2-Dihydronaphthalene to Tetracyanoethene
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The hydrogen transfer between 1,2-dihydronaphthalene (1) and tetracyanoethene (2) is highly stereoselective.Kinetic isotope effects exclude an electrocyclic reaction and support an ionic multistep mechanism.Stereoselectivity is caused by steric fixation in the intermediate ion pair.
- Heesing, Albert,Muellers, Wolfgang
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