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Cas Database

121-46-0

121-46-0

Identification

  • Product Name:2,5-Norbornadiene

  • CAS Number: 121-46-0

  • EINECS:204-472-0

  • Molecular Weight:92.1405

  • Molecular Formula: C7H8

  • HS Code:29021990

  • Mol File:121-46-0.mol

Synonyms:2,5-Norbornadiene(8CI);3,6-Methano-1,4-cyclohexadiene;Bicyclo[2.2.1]heptadiene;NSC 13672;Norbornadiene;Bicyclo[2.2.1]hepta-2,5-diene;

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Safety information and MSDS view more

  • Pictogram(s):FlammableF

  • Hazard Codes:F

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapour

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. Excerpt from ERG Guide 128P [Flammable Liquids (Water-Immiscible)]: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 2016)

  • Fire-fighting measures: Suitable extinguishing media Excerpt from ERG Guide 128P [Flammable Liquids (Water-Immiscible)]: CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. CAUTION: For mixtures containing alcohol or polar solvent, alcohol-resistant foam may be more effective. SMALL FIRE: Dry chemical, CO2, water spray or regular foam. LARGE FIRE: Water spray, fog or regular foam. Do not use straight streams. Move containers from fire area if you can do it without risk. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2016) Excerpt from ERG Guide 128P [Flammable Liquids (Water-Immiscible)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. Substance may be transported hot. For hybrid vehicles, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. If molten aluminum is involved, refer to ERG Guide 169. (ERG, 2016) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
  • Product Description:Norbornadiene
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  • Manufacture/Brand:TRC
  • Product Description:2,5-Norbornadiene (stabilized with BHT)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2,5-Norbornadiene (stabilized with BHT) >97.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2,5-Norbornadiene (stabilized with BHT) >97.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2,5-Norbornadiene (stabilized with BHT) >97.0%(GC)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Bicyclo[2.2.1]hepta-2,5-diene 98%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Bicyclo[2.2.1]hepta-2,5-diene 98%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2,5-Norbornadiene (stabilised) for synthesis. CAS 121-46-0, molar mass 92.14 g/mol., (stabilised) for synthesis
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  • Product Description:2,5-Norbornadiene (stabilised) for synthesis
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Bicyclo[2.2.1]hepta-2,5-diene 98%
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Relevant articles and documentsAll total 69 Articles be found

SURFACE PHOTOCHEMISTRY: SEMICONDUCTOR PHOTOINDUCED VALENCE ISOMERIZATION OF QUADRICYCLANE TO NORBORNADIENE

Draper, Anthony M.,Mayo, Paul de

, p. 6157 - 6160 (1986)

Contrary to a recent report, the valence isomerization via a radical cation, of quadricyclane to norbornadiene on the surface of illuminated CdS and ZnO is described.

-

Westberg,Dauben

, p. 5123 (1968)

-

Iridium-Catalyzed Asymmetric Hydroalkenylation of Norbornene Derivatives

Sun, Xin,Bai, Xiao-Yan,Li, An-Zhen,Li, Bi-Jie

, p. 2182 - 2187 (2021)

Transition-metal-catalyzed asymmetric hydroalkenylation of alkenes provides an atom-economical method to build molecular complexity from easily available materials. Herein we report an iridium-catalyzed asymmetric hydroalkenylation of unconjugated alkenes with acrylamides and acrylates. The catalytic hydroalkenylation of norbornene derivatives occurred to form products with allylic stereocenters with high chemo-, regio-, and stereoselectivities. DFT calculations revealed that the migratory insertion is irreversible and the enantiodetermination step.

DIOXIRANES: DIMETHYLDIOXIRANE CATALYZED VALENCE ISOMERIZATION OF QUADRICYCLANE

Murray, Robert W.,Pillay, M. Krishna

, p. 15 - 18 (1988)

Dimethyldioxirane, 3, catalyzes the isomerization of quadricyclane to norbornadiene.Turnover numbers up to 60 have been measured.The unusual orbital occupancy in 3 may be responsible for these observations.

Structure-Reactivity Factors for Exciplex Isomerization of Quadricyclene and Related Compounds

Jones, Guilford,Chiang, Sheau-Hwa,Becker, William G.,Greenberg, Don P.

, p. 681 - 683 (1980)

The quadricyclenes (1) and (3) are equally effective in exciplex isomerization although other cage hydrocarbons do not undergo efficient reaction when sensitized by aromatic fluorophores; irradiation of charge-transfer complexes of (1) and (3) and electron-deficient alkenes results in efficient valence but not geometrical isomerization.

Electron transfer induced deazatization of cyclic Azo derivatives of quadricyclane and norbornadiene

Sluggett, Gregory W.,Turro, Nicholas J.,Roth, Heinz D.

, p. 9982 - 9989 (1995)

The photosensitized oxidation of two cyclic azoalkane derivatives (Azo-Q, Azo-N) of quadricyclane (Q) and norbornadiene (N) has been investigated using steady-state and laser flash photolysis techniques as well as chemically induced dynamic nuclear polarization (CIDNP). Irradiation of acetonitrile solutions of 9,10-dicyanoanthracene (DCA), 2,6,9,10-tetracyanoanthracene (TCA), or chloranil (Chl) in the presence of Azo-Q results in rapid and efficient deazatization to afford N. Similar irradiation of DCA, TCA, and Chl in the presence of Azo-N yields N and Q. CIDNP experiments reveal that polarized N is formed as a cage product in the Chl sensitized photolysis of Azo-Q while polarized N and Q are both formed as cage products from Azo-N. The results are consistent with competitive fragmentation of Azo-N?+ to N?+ and Q?+, and selective deazatization of Azo-Q?+ to N?+. Irradiation of 1-cyanonaphthalene in the presence of Azo-Q or Azo-N affords Q and/or N in chemical yields similar to those obtained from direct and naphthalene sensitized irradiations, indicative of singlet energy transfer quenching. Bimolecular rate constants for quenching by Azo-N and Azo-Q were determined by steady-state fluorescence methods for singlet sensitizers, or by laser flash photolysis (LFP) for 3Chl*.

-

Wiberg,Connon

, p. 5411,5412 (1976)

-

New quadricyclane-based cyclic polycarbosilanes

Gringolts,Bermeshev,Kaz'Min,Finkelshtein

, p. 49 - 51 (2009)

-

THERMAL ISOMERIZATION OF QUADRICYCLANE TO NORBORNADIENE CATALYZED BY COPPER(II) AND TIN(II) SALTS.

Fife,Morse,Moore

, p. 7404 - 7407 (1983)

Copper(II) salts and tin(II) chloride show exceptional heterogeneous catalytic behavior in converting quadricyclane to norbornadiene in benzene. The heterogeneous catalysis mechanism is described by the adsorption of quadricyclane on the salt surface by a combination of a one-site and a two-site coordination. The two-site-coordination process results in the formation of C//7H//8X//2 (X equals Cl or Br) as a side product when CuCl//2 or CuBr//2 are used as catalysts. The rate constant for the disappearance of quadricyclane is much greater when CuCl//2 or CuBr//2 are used as catalysts. The rate constant for the disappearance of quadricyclane is much greater when CuCl//2 or CuBr//2 (approximately 10** minus **2 min** minus **1 cm** minus **2) is used than when CuSO//4 (approximately 10** minus **4 min** minus **1 cm** minus **2) is used.

PHOTOISOMERIZATION OF NORBORNADIENE TO QUADRICYCLANE IN THE PRESENCE OF COPPER(I)-NITROGEN LIGAND CATALYSTS

Maruyama, Kazuhiro,Terada, Kazutoshi,Naruta, Yoshinori,Yamamoto, Yoshinori

, p. 1259 - 1262 (1980)

Use of copper(I)-nitrogen ligand catalysts, such as Ph3PCuCl.bipy (1), Ph3PCuCl.phen (2), Ph3PCuCl.phtha (3), and Ph3PCuBr.py (4), enables the photochemical isomerization of norbornadiene to quadricyclane in longer wavelength than 350 nm, in which CuCl catalyst itself can not induce such an isomerization.

PHOTOGENERATED CATALYSIS BY TRANSITION-METAL COMPLEXES. PHOTOACCELERATION OF THE VALENCE ISOMERIZATION OF QUADRICYCLENE TO NORBORNADIENE IN THE PRESENCE OF PdCl2( eta 4-NORBORNADIENE).

Borsub,Kutal

, p. 4826 - 4828 (1984)

Light accelerates the rate at which PdCl//2( eta **4-NBD) (1) catalyzes the valence isomerization of quadricyclene (Q) to norbornadiene (NBD). The observed quantum yield, defined as (mol of NBD produced/mol of photons absorbed), can exceed 10**2 and is dependent upon Q concentration, light intensity, and solvent. Several lines of evidence are consistent with the intermediacy of radical species in the isomerization process. The results are discussed in terms of a redox-chain mechanism in which the initiation step involves reductive quenching of a Pd-to-NBD charge-transfer excited state of 1 by Q.

Organic Photochemistry with 6.7 eV Photons: Tetracyclo2,7.04,6>heptane (Quadricyclene)

Srinivasan, Ra.,Baum, Thomas,Epling, Gary

, p. 437 - 438 (1982)

Irradiation of quadricyclene in solution leads to isomeric products in addition to bicyclohepta-2,5-diene, which reduces its usefulness in solar energy storage.

Chemistry of Weakly Solvated Lanthanide-Metal Cations. Synthesis, Characterization, and Catalytic Chemistry of x

Thomas, Richard R.,Chebolu, Venkatasuryanarayana,Sen, Ayusman

, p. 4096 - 4103 (1986)

The title compound, x, 1, was synthesized by the NOBF4 oxidation of metallic Eu in CH3CN.The interaction of the BF4- ions with the Eu(III) center was established by molecular weight, conductivity, and 11B and 19F NMR spectral measurements. 1 was found to exist as a dimer in CH3CN.In addition, it behaved as a 1:2 electrolyte, indicating the coordination of two of the BF4- ions per Eu(III) ion.However, the conductivity increased when chelating amines were added due to the partial displacement of the coordinated BF4- ions.The 11B and 19F NMR spectra of 1 in CH3CN indicated the presence of two different types of BF4- anions, one of which was isotropically shifted due to interaction with the paramagnetic Eu(III) center.The coordinated BF4- anions could be displaced quantitatively by the addition of 2 equiv of NO3- ions per Eu(III) ion.A degenerate metathesis of the fluorine between the BF3 and the coordinated BF4- ions was observed when BF3 was added to a CH3CN solution of 1. 1 formed a charge-transfer complex with tetra-p-anisylethylene in CH3NO2 but not in CH3CN.In addition, 1 initiated the oligomerization and the polymerization of styrene, α-methylstyrene, and 1,3-cyclohexadiene in CH3NO2.The molecular weights of the polymers obtained increased markedly on lowering the reaction temperature.At room temperature, indan derivatives were obtained from α-methyl- and α-phenylstyrene.The rate of polymerization of styrene was markedly attenuated when CH3CN was used instead of CH3NO2. 1 also initiated the isomerization of quadricyclane and the ring-opening polymerization of 2(10)-pinene and cyclopropylbenzene in CH3NO2.

Synthesis of tricyclononenes and tricyclononadienes containing MX 3-groups (M=C, Si, Ge; X=Cl, Me)

Bulgakov,Bermeshev,Demchuk,Lakhtin,Kazmin,Finkelshtein, E.Sh.

, p. 2166 - 2171 (2012)

A series of new organoelement-substituted (Si-, Ge-) tricyclononenes and tricyclononadienes was obtained via the [2σ+2σ+2π]-cycloaddition reaction of the corresponding substituted ethylenes and acetylenes with quadricyclane. The chemical behavior of Si-, Ge-, Sn-containing olefins and acetylenes under the cycloaddition conditions was studied.

Fourier transform near-infrared absorption spectroscopic study of catalytic isomerization of quadricyclane to norbornadiene by copper(II) and tin(II) salts

Chuang, Eric Chau-Chin,Lin, King-Chuen

, p. 132 - 136 (2002)

By using Fourier transform near-infrared (NIR) absorption spectroscopy, we have investigated the catalytic conversion of quadricyclane to norbornadiene. Either CuSO4 in chloroform or SnCl2 in benzene is used as catalyst. To avoid the effect of sample heterogeneity, the reaction mixture is kept still without stirring. The NIR light beam is guided to propagate through the solution right above the surface of metal salt. The NIR absorption spectra are acquired at 5-min intervals for a reaction period of 6 h. The related concentrations of quadricyclane and norbornadiene in the temporal evolution are determined with the method of partial least squares. A kinetic model for the pseudo-first-order reaction is derived considering the diffusion motion. Accordingly, the second-order rate constant for the isomerization catalyzed by CuSO4 and SnCl2, respectively, are determined to be (1.38 ?± 0.04) ?? 10-3 and (4.62 ?± 0.09) ?? 10-3 min-1 g-1. The norbornadiene is produced via a one-site coordination between the reactant and the catalyst. The product contribution from the intermediate of a two-site coordination is negligible in our system. The obtained result for CuSO4 is comparable with that detected by using Raman spectroscopy.

-

Tremelling et al.

, p. 3119 (1977)

-

Valence Isomerization of Quadricyclene Mediated by Illuminated Semiconductor Powders

Ikezawa, Hideo,Kutal, Charles

, p. 3299 - 3303 (1987)

Quadricyclene undergoes valence isomerization to norbornadiene in the presence of photoexcited n-type semiconductor powders.For samples irradiated under comparable conditions of time and intensity, the yield of the diene product varies with (i) the semiconductor in the order CdS > TiO2 > ZnO and (ii) the solvent in the order dichloromethane > acetonitrile > tetrahydrofuran.The presence of oxygen in a sample diminishes the product yield, whereas both methylviologen dication and diphenylamine enhance the yield.The quantum efficiency of norbornadiene production appearsto be rather low (ca. 10-2 for CdS) in these heterogeneous systems.These observations are interpreted in terms of the redox chemistry that results upon interaction of the photogenerated electron-hole pairs in the semiconductor with the surrounding organic medium.

LiCB11Me12: A catalyst for pericyclic rearrangements

Moss, Stefan,King, Benjamin T.,De Meijere, Armin,Kozhushkov, Sergei I.,Eaton, Philip E.,Michl, Josef

, p. 2375 - 2377 (2001)

(matrix presented) Benzene and 1,2-dichloroethane solutions of the Li+ salt of the weakly coordinating anion CB11Me12- catalyze the rearrangement of cubane to cuneane, quadricyclane to norbornadiene, basketene to Nenitzescu's hydrocarbon, and diademane to triquinacene. The Claisen rearrangement of phenyl allyl ether is also strongly accelerated.

-

Hogeveen,Nusse

, p. 3667,3668 (1973)

-

-

Wilson,Rinker

, p. 268 (1975)

-

Overtone Vibrational Photochemistry of Quadricyclane

Lishan, David G.,Reddy, K. V.,Hammond, George S.,Leonard, Jack E.

, p. 656 - 660 (1988)

The photochemistry of quadricyclane (Q) was explored by single-photon excitation to high vibrational levels.Spectra of the ν = 4-7 carbon-hydrogen overtones were recorded by using intracavity absorption and photoacoustic detection.These spectra were compared to the infrared fundamental spectrum and assigned.Excitation of the ν = 5 and ν = 6 bands of cyclopropanoid and methylenic hydrogens leads to reaction.At least one intermediate, probably a vibrationally excited form of norbornadiene (N), must be involved because partitioning among various reaction channels is pressure dependent.Apparent rate constants were measured and correlated with variations in pressure according to the Stern-Volmer relationship.Experimental values were compared with rate constants calculated by RRKM theory.Although there is a modest amount of "excess" reaction observed for the lowest excitation energies above threshold, overall evaluation provides no significant evidence for concentration of energy in localized modes for times that are long compared with reaction times.

-

Mango

, p. 505,506-508 (1971)

-

Kinetics of the Isomerization of Quadricyclane to Norbornadiene Promoted by Tin(II) Chloride and Palladium(II) Chloride

Patrick, Timothy B.,Bechtold, Dana S.

, p. 1935 - 1937 (1984)

The conversion of quadricyclane to norbornadiene is promoted by both SnCl2 and PdCl2.The SnCl2 reaction occurs by a second-order process with activation parameters of ΔG(excit.), ΔH(excit.), and ΔS(excit.) of 22.5 kcal/mol, 13.9 kcal/mol, and -28.7 eu, respectively.The PdCl2-promoted reaction occurs by formation of an equilibrium species and follows Michaelis-Menton kinetics.A theoretical interpretation based on the Dewar-Duncanson model of bonding of metal ions with olefins is used to describe possible mechanistic differences in the reactions.

Kinetics of catalytic isomerization of quadricyclane to norbornadiene using near infrared absorption spectroscopy: Conversion rate and diffusion motion in heterogeneous reaction

Fan, Hsiu-Fang,Chin, Thou-Long,Lin, King-Chuen

, p. 9364 - 9370 (2004)

By use of Fourier transform near-infrared (NIR) absorption spectroscopy and the aid of a kinetic model, we have investigated the conversion of quadricyclane to norbornadiene catalyzed by anhydrous CuSO4 and SnCl2 in chloroform. The reaction mixture is not agitated so as to avoid the effect of sample heterogeneity. The NIR absorption spectra are acquired, at a position a??2 mm above the catalyst surface, at 30-s intervals during 4 h. The concentrations of quadricyclane and norbornadiene are determined with the analysis of partial least squares. The isomerization of quadricyclane, as numerically solved from the model, is expected to describe its behavior more accurately in the catalytic system than that obtained previously. In addition to the isomerization rate, the kinetic model takes into account the contribution of diffusion. The diffusion coefficients of quadricyclane can be determined to be 3.8 ?? 10-5 cm2 s-1 in chloroform and 1.14 ?? 10-5 and 2.85 ?? 10-6 cm2 s-1 inside the CuSO4 and SnCl2 stacks, respectively. Diffusion is slowed inside the solid stacks, and thus the molecular mechanism cannot be suitable for this system. Given the diffusion coefficients, the pseudo-first-order depletion rate constants are evaluated to be (3.7 ?± 0.1) ?? 10-3 and (3.8 ?± 0.1) ?? 10-3 s-1 for CuSO4 and SnCl2, respectively. The corresponding second-order rate constants are determined to be (1.3 ?± 0.2) ?? 10-5 and (2.0 ?± 0.1) ?? 10-6 s-1 A-1 by considering the density and the size of the catalyst particles; A denotes the total catalyst surface area per unit effective volume of solvent. The rate constant with the CuSO4 catalyst is consistent with others obtained in a continuously stirred mixture. In the surface-mediated reaction, the catalytic isomerization is subject to one-site coordination (1:1 complex) between the reactant and the catalyst. Nevertheless, a two-site coordinated reaction cannot be excluded unless the interstitial size dependence of the depletion rate is known.

Triplex Promoted Intersystem Crossing of Ion-Radical pairs in the Photosensitized Valence Isomerization of Quadricyclane: Chemically Induced Dynamic Nuclear Polarization (CIDNP) Evidence

Yang, Li,Zhang, Mao-Xi,Liu, You-Cheng,Liu, Zhong-Li,Chow, Yuan L.

, p. 1055 - 1056 (1995)

Photosensitized valence isomerization of quadricyclane to norbornadiene by dibenzoylmethanatoboron difluoride in the presence of durene shows a CIDNP effect which is opposite in direction to that occurring in the absence of durene, demonstrating possible participation of triplexes in the durene co-sensitized reaction.

-

Walsh,Wells

, p. 319 (1975)

-

Reactions of Quadricyclane with Sulphur Dioxide: Formation of a Stable β-Sultine and Catalysed Isomerization to Norbornadiene

Lucchi, Ottorino De,Lucchini, Vittorio

, p. 464 - 465 (1982)

Sulphur dioxide, as solvent or in chloroform, catalyses the isomerization of quadricyclane (1) to norbornadiene and cycloadds to (1) to afford exo-3-oxa-4-thiatricyclo2,5>non-7-ene 4-oxide (3); in the presence of a deficiency of sulphur dioxide, (3) is remarkably stable in solution, but decomposes rapidly as pure product.

The Radical Cations of Bicyclohepta-2,5-diene (8,9,10-Trinorborna-2,5-diene) and Bicycloocta-2,5-diene (2,3-Dihydrobarrelene). An ESR and ENDOR Study

Gerson, Fabian,Qin, Xue-Zhi

, p. 383 - 390 (1989)

The radical cation of bicyclohepta-2,5-diene (8,9,10-trinorborna-2,5-diene; 1) in CF2ClCFCl2 and CF3CCl3 matrices and that of bicycloocta-2,5-diene (2,3-dihydrobarrelene; 2) in CFCl3 and CF3CCl3 matrices have been studied by ESR and ENDOR spectroscopy.For 1+., the coupling constants of the olefinic, methano-bridge, and bridgehead protons are -0.780 +/- 0.005, +0.304 +/- 0.002, and -0.049 +/- 0.002 mT, respectively.The hyperfine tensor for the methano-bridge protons is axial.A = +0.263 +/- 0.002 and A = +0.386 +/- 0.002 mT, while that for the olefinic protons is orthorhombic, Ax = -0.594 +/- 0.005, Ay = -0.913 +/-0.005, and Az = -0.834 +/- 0.005 mT (x parallel to C-H bond, z parallel to 2p? axis).For 2+., the coupling constants of the olefinic, ethano-bridge, and bridgehead protons are -0.68 +/- 0.01, +0.162 +/- 0.005, and -0.108 +/- 0.005 mT, respectively.The hyperfine data for 1+. and 2+. fully support the presentation of their singly occupied orbitals as antisymmetric combinations, b2(?), of the two bonding ethene ?-MO's.

-

Frey

, p. 365 (1964)

-

Carbenes and the O-H Bond: Norbornenylidenes

Kirmse, Wolfgang,Meinert, Thomas

, p. 1065 - 1066 (1994)

Bicyclohept-2-en-7-ylidene 10 and bicyclohept-5-en-2-ylidene 21 are shown to react with methanol by way of proton transfer, with formation of norbornenyl cations.

Rhodium(I) complexes of the conformationally rigid IBioxMe4 ligand: Preparation of mono-, bis-, and tris-ligated NHC complexes

Chaplin, Adrian B.

, p. 3069 - 3077 (2014)

The preparation and characterization of a series of mono-, bis-, and tris-ligated rhodium(I) complexes of Glorius' conformationally rigid bioxazoline-derived N-heterocyclic carbene ligand IBioxMe4 are described. Through reaction of [Rh(COE)2Cl]2 (COE = cis-cyclooctene) with isolated IBioxMe4, [Rh(IBioxMe 4)(COE)Cl]2 (1), trans-[Rh(IBioxMe4) 2(COE)Cl] (2), and [Rh(IBioxMe4)3Cl] (3) were each isolated by careful choice of the reaction conditions. Further substitution and salt metathesis reactions of 1-3 were investigated, and derivatives containing CO, norbornadiene, and cyclopentadienyl ancillary ligands were readily isolated. Notably, halide abstraction from 2 and 3 using Na[BAr F4] (ArF = 3,5-C6H 3(CF3)2) resulted in the formation of low-coordinate T-shaped cis-[Rh(IBioxMe4)2(COE)][BAr F4] (9) and [Rh(IBioxMe4)3][BAr F4] (11). The solid-state structures of 2, 9, and 11 each feature IBioxMe4 ligands that bind unusually with tilted coordination geometries.

COBALT(II)TETRAPORPHYRIN-CATALYZED ISOMERISATION OF ELECTRONEGATIVE SUBSTITUTED QADRICYCLANES

Miki, Sadao,Ohno, Toshinobu,Iwasaki, Hideaki,Yoshida, Zen-ichi

, p. 3487 - 3490 (1985)

Co(II)TPP-catalyzed isomerisation of a series of electronegative substituted quadricyclanes(1) to the corresponding norbornadiene(2) was found to proceed via radicophilic attack of the metal to 1.

Alumina-Anchored Cobalt Porphine Catalysts for the Conversion of Quadricyclane to Norbornadiene

Miki, Sadao,Asako, Yoshinobu,Morimoto, Masayoshi,Ohno, Toshinobu,Yoshida, Zen-ichi,et al.

, p. 973 - 982 (1988)

Methods are described for the preparation of cobalt(II) deuteroporphyrin and cobalt(II) tetrakis(p-sulfonatophenyl)porphine anchored on alumina beads coated with polyaminesulfone-A.Wavelength dispersive X-ray microanalysis showed that the cobalt(II) porphine distributes within the catalyst outer surface layer of ca. 100 μm depth.The catalysts are highly active for the cycloreversion of quadricyclane to norbornadiene.A detailed kinetics of the isomerization using an isothermal recycle reactor gave a rate expression of Langmuir-Hinshelwood type.The catalysts gradually lose their activity, which can be regenerated completely by heating the catalysts at 200 deg C in vacuo.

Collisional activation of quadricyclane by azulene: An example of very strong collisions

Hassoon, S.,Oref, I.,Steel, C.

, p. 1743 - 1744 (1988)

-

-

Walsh,Wells

, p. 149,150, 151 (1975)

-

ELECTROCHEMICAL CATALYSIS OF THE VALENCE ISOMERIZATION OF QUADRICYCLENE

Yasofuku, Katsutoshi,Takahashi, Katsuo,Kutal, Charles

, p. 4893 - 4896 (1984)

Electrochemical oxidation of quadricyclene results in its isomerization to norbornadiene by a redox chain mechanism.

-

Herndon,Lowry

, p. 1922 (1964)

-

TRANSFORMATIONS OF TETRACYCLO2,7.04,6>HEPTANE (QUADRICYCLANE) CATALYZED BY Pd2+ AND Pd0 COMPLEXES

Khusnutdinov, R. I.,Dokichev, V. A.,Popova, I. O.,Nefedov, O. M.,Tolstikov, G. A.,Dzhemilev, U. M.

, p. 433 - 435 (1985)

-

Thermal Decomposition of a Series of 1,2-Diazetines

Breton, Gary W.,Shugart, John H.

, p. 8643 - 8649 (2003)

A homologous series of tricyclic diazetines (6a-c), differing by the number of methylene groups in the saturated bridges of the fused carbon bicycles, was synthesized. The ΔH? of decomposition for each of the diazetines to afford N2 and the corresponding alkene was determined experimentally: 6a, 31.7; 6b, 39.3; 6c, 38.8 kcal/mol. The ground-state strain energy of each diazetine was estimated utilizing computationally obtained ΔHf's for each of the experimentally investigated diazetines as well as several other diazetines whose ΔH?'s had been previously reported in the literature. The sum of the ground-state strain energies and ΔH?'s of decomposition for all of the diazetines was nearly constant, with an average value of 59 kcal/mol, suggesting that all of the diazetines decompose via the same mechanism. Generally, the higher the ground-state strain energy of the diazetine, the less the ΔH? for decomposition. The decomposition transition states for 6a-c and 7 were modeled computationally at the RB3LYP/6-311+G(3df,2p)//UB3LYP/6-31+G(d,p) level. The agreement of the experimentally determined ΔH? values with transition-state energies obtained computationally supports the reaction mechanism originally proposed by Yamabe that the elimination process occurs by an unsymmetrical, yet concerted, transition state with strong biradical character.

Endo entry to the nortricyclyl-norbornenyl cation system: Stereochemistry in the fragmentation of endo-5-norbornenyl-2-oxychlorocarbene

Moss, Robert A.,Fu, Xiaolin,Sauers, Ronald R.,Wipf, Peter

, p. 8454 - 8460 (2005)

Fragmentation of (S)-endo-5-norbornenyl-2-oxychlorocarbene [(S)-8] in cyclohexane-d12 gives ~20% (S)-endo-2-chloro-5-norbornene [(S)-7] with ~50% ee, 65-70% (R)-exo-2-chloro-5-norbornene [(R)-4] with >95% ee, and ~12% (R)-3-nortricyclyl chloride [(R)-5] with ~22% ee. (Analogous stereochemical results were also obtained starting with the enantiomeric carbene (R)-8.) The (S)-8 to (S)-7 and (S)-8 to (R)-4 conversions are ascribed mainly to retention and inversion SNi transition states, respectively. These have been located by computational methods and are nearly isoenergetic. In more polar solvents (CDCl3 and CD3CN), the fragmentation of (S)-8 increasingly occurs via competitive ion pair pathways in which steroselectivity is diminished, and escape to the norbornenyl-nortricyclyl cation directs the products away from endo-2-chloro-5-norbornene toward exo-chloride 4 and nortricyclyl chloride 5.

Cycloreversion of Quadricyclane to Norbornadiene Catalyzed by Tin (II) Complexes

Landis, M.E.,Gremaud, D.,Patrick, T.B.

, p. 375 - 378 (1982)

The conversion of quadricyclane (1) to norbornadiene (2) is catalyzed by stannous chloride and stannous chloride-phosphine complexes.A newly synthesized polymer-bound phosphine-stannous chloride complex also proved effective in the catalytic conversion 1 to 2.

Pyrolysis of Bicycloheptane-2-thiols: Evidence for a Carbene Intermediate in a Thermal Hydrogen Sulphide Elimination

Johnson, Douglas E.,Dimian, Adel F.

, p. 416 - 417 (1987)

Pyrolysis of endo- and exo-bicycloheptane-2-thiols yields tricyclo2,6>heptane and bicyclohept-2-ene via competing carbene and radical mechanisms.

Abel, E. W.,Bennet, M. A.,Wilkinson, G.

, (1959)

Rh(III)-photosensitized interconversion of norbornadiene and quadricyclane

Sluggett, Gregory W.,Turro, Nicholas J.,Roth, Heinz D.

, p. 8834 - 8838 (1997)

The utility of two Rh(III) diimine complexes, Rh(phen)33+ and Rh(phi)2(phen)3+ (phen = 1,10-phenanthroline, phi = 9,10-phenanthrenequinone diimine), as sensitizers for the interconversion of norbornadiene (N) and quadricyclane (Q) has been investigated using steady-state photochemical and laser flash photolysis (LFP) techniques. Irradiation of acetonitrile solutions of Rh(phen)33+ and N causes slow conversion to Q. The reaction is reversible; irradiation of Rh(phen)33+ in the presence of Q leads to N. Irradiation of acetonitrile solutions of Rh(phi)2(phen)3+ and Q yields N. However, this reaction is irreversible; irradiation of the Rh-(III) complex in the presence of N fails to afford Q. Irradiation of methanol solutions of either Rh(III) complex in the presence of N or Q affords minor amounts of two methanol-C7 adducts but fails to quench the N-Q interconversion reaction. The results are consistent with N-Q interconversion via an exciplex intermediate. The Rh(III)-sensitized deazatization of two cyclic azoalkane derivatives (Azo-N, Azo-Q) of N and Q was also investigated. Deazatization was achieved by Rh(phen)33+ but not Rh(phi)2(phen)3+ sensitization. The results are consistent with a mechanism involving triplet energy transfer, but the involvement of exciplex intermediates cannot be ruled out. Bimolecular rate constants for quenching of the Rh(III) excited states by N, Q, Azo-N, and Azo-Q were determined by LFP.

-

Murov et al.

, p. 2957 (1968)

-

Photosensitization of Quadricyclene Isomerization by Electron Acceptors. A Short-Circuit Nonradiative Decay Mechanism for Electron Donor-Acceptor Quenching in Polar Media

Jones, Guilford,Chiang, Sheau-Hwa,Becker, William G.,Welch, Jeanne A.

, p. 2805 - 2808 (1982)

Quantum efficiences are reported for valence isomerization of quadricyclene to norbornadiene induced on quenching the excited singlet state of electron acceptor sensitizers.The notable feature is the large reduction in yield of isomerization in a polar solvent (acetonitrile) compared with reported data for similar photolysis in nonpolar media.A comparison of isomerization yields and flash photolysis results based on the mode of sensitization (i.e., singlet quenching vs. triplet quenching vs. excitation of ground-state charge-transfer complexes) leads to a distinction among exciplex, contact ion pair, and solvent-separated ion-pair intermediates which are potentially involved in electron donor-acceptor quenching.

PHOTOINDUCED ADDITION OF NUCLEOPHILES TO BICYCLOHEPTA-2,5-DIENE

Gassman, Paul G.,Olson, Kurt D.

, p. 19 - 22 (1983)

The 1-cyanonaphthalene photosensitized addition of water and methanol to the cation-radical of bicyclohepta-2,5-diene is described.

Catalytic carbonylative rearrangement of norbornadiene via dinuclear carbon-carbon oxidative addition

Hartline, Douglas R.,Zeller, Matthias,Uyeda, Christopher

supporting information, p. 13672 - 13675 (2017/11/07)

Single bonds between carbon atoms are inherently challenging to activate using transition metals; however, ring-strain release can provide the necessary thermodynamic driving force to make such processes favorable. In this report, we describe a strain-induced C-C oxidative addition of norbornadiene. The reaction is mediated by a dinuclear Ni complex, which also serves as a catalyst for the carbonylative rearrangement of norbornadiene to form a bicyclo[3.3.0] product.

REDOX-AUXILIARY CATALYSIS

-

Paragraph 0007; 0101, (2015/05/26)

Disclosed herein is a method of activating a compound for a chemical reaction comprising functionalizing a compound with a redox auxiliary group and oxidizing the redox auxiliary group that is bonded to the compound, thereby activating the compound, wherein the activated compound undergoes a chemical reaction to form a product and the oxidation of the redox auxiliary group is reversible. Methods of making and using these materials are also disclosed.

Solar driven uphill conversion of dicyclopentadiene to cyclopentadiene: An important synthon for energy systems and fine chemicals

Dinda, Milan,Chakraborty, Supratim,Kanti Si, Mrinal,Samanta, Supravat,Ganguly, Bishwajit,Maiti, Subarna,Ghosh, Pushpito K.

, p. 54558 - 54564 (2015/02/05)

The retro Diels-Alder conversion of endo-dicyclopentadiene to cyclopentadiene (Cp)-which is thermodynamically uphill under ambient conditions (ΔG = +9.7 kcal mol-1; values based on computation at 273 K following CBS-QB3 methodology)-was carried out at 175-190 °C in neat state using solar energy. The reaction is thermodynamically favorable at elevated temperature. Considering heat release from the reverse reaction (ΔH = -23.4 kcal mol-1), the energy storage efficiency was computed to be ca. 5.5% with respect to the IR component in concentrated solar radiation. Solar energy was further utilized for preparation of a model 2,5-norbornadiene derivative (75% isolated yield) through the cycloaddition reaction of Cp with 4-phenylbut-3-yn-2-one at 150-185 °C. The norbornadiene-quadricyclane system has been proposed for solar energy storage, and its solar assisted synthesis would help reduce its carbon footprint over its life cycle. Norbornadiene synthesis using solar energy may also be of interest for greener processing of fuels derived from this compound. Cookson's cage ketone, which too has been proposed as an energy storage medium, was additionally synthesized from the Diels-Alder adduct of Cp and p-benzoquinone employing concentrated solar photo-thermochemical conditions. The reaction proceeded rapidly (15 min) and gave the desired product in 96% isolated yield. Besides the above applications, Cp is an important synthon in the preparation of fine chemicals.

Process route upstream and downstream products

Process route

exo-3,4-diazotricyclo[4.2.1.0<sup>2,5</sup>]nona-3,7-diene
23979-29-5

exo-3,4-diazotricyclo[4.2.1.02,5]nona-3,7-diene

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

quadricyclo[2.2.1.0.0]heptane
278-06-8

quadricyclo[2.2.1.0.0]heptane

Conditions
Conditions Yield
With 9,10-Dicyanoanthracene; Irradiation;
With 9,10-Dicyanoanthracene; In acetonitrile; at 23 ℃; Product distribution; Mechanism; Irradiation; var. sensitizers and solvents;
In various solvent(s); at 144.85 ℃; Further Variations:; Temperatures; Kinetics;
3,4-diazaquadricyclo<6.1.0.0<sup>2,6</sup>.0<sup>5,9</sup>>non-3-ene

3,4-diazaquadricyclo<6.1.0.02,6.05,9>non-3-ene

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

quadricyclo[2.2.1.0.0]heptane
278-06-8

quadricyclo[2.2.1.0.0]heptane

Conditions
Conditions Yield
With 9,10-Dicyanoanthracene; In acetonitrile; at 23 ℃; Product distribution; Mechanism; Irradiation; var. sensitizers and solvents;
syn-Tricyclo<3.2.0.0<sup>2,4</sup>>hept-6-en
39521-78-3,79356-83-5,79356-84-6

syn-Tricyclo<3.2.0.02,4>hept-6-en

bicyclo[3.2.0]hepta-2,6-diene
2422-86-8

bicyclo[3.2.0]hepta-2,6-diene

Cyclohepta-1,3,5-triene
544-25-2

Cyclohepta-1,3,5-triene

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

anti-Tricyclo<3.2.0.0<sup>2,4</sup>>hept-6-en
39521-78-3,79356-83-5,79356-84-6

anti-Tricyclo<3.2.0.02,4>hept-6-en

quadricyclo[2.2.1.0.0]heptane
278-06-8

quadricyclo[2.2.1.0.0]heptane

Conditions
Conditions Yield
In 2,2,4-trimethylpentane; at 119.5 ℃; for 1.5h; Product distribution; Thermodynamic data; Rate constant; Ea, ΔH*, ΔS*;
15.7 % Chromat.
22.9 % Chromat.
31.1 % Chromat.
15.9 % Chromat.
2,3-dibromobicyclo[2.2.1]heptane
60154-53-2

2,3-dibromobicyclo[2.2.1]heptane

norborn-2-ene
498-66-8

norborn-2-ene

exo-2-ethoxybicyclo[2.2.1]heptane
25273-25-0

exo-2-ethoxybicyclo[2.2.1]heptane

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

5-ethoxybicyclo[2.2.1]hept-2-ene

5-ethoxybicyclo[2.2.1]hept-2-ene

Conditions
Conditions Yield
With ethanol; zinc; at 78 ℃; for 6h; Title compound not separated from byproducts;
21 % Chromat.
42 % Chromat.
13 % Chromat.
24 % Chromat.
With ethanol; zinc; for 6h; Title compound not separated from byproducts;
24 % Chromat.
42 % Chromat.
13 % Chromat.
21 % Chromat.
ethanol
64-17-5

ethanol

2,3-dibromobicyclo[2.2.1]heptane
60154-53-2

2,3-dibromobicyclo[2.2.1]heptane

norborn-2-ene
498-66-8

norborn-2-ene

exo-2-ethoxybicyclo[2.2.1]heptane
25273-25-0

exo-2-ethoxybicyclo[2.2.1]heptane

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

5-ethoxybicyclo[2.2.1]hept-2-ene

5-ethoxybicyclo[2.2.1]hept-2-ene

Conditions
Conditions Yield
With zinc; for 6h;
24 % Chromat.
21 % Chromat.
42 % Chromat.
13 % Chromat.
With zinc; for 6h; Title compound not separated from byproducts;
24 % Chromat.
21 % Chromat.
13 % Chromat.
42 % Chromat.
endo-bicyclo<2.2.1>heptane-2-thiol

endo-bicyclo<2.2.1>heptane-2-thiol

norbornene
498-66-8

norbornene

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

tricyclo<2.2.1.0<sup>2,6</sup>>heptane
279-19-6

tricyclo<2.2.1.02,6>heptane

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

Conditions
Conditions Yield
In benzene; at 400 ℃; under 760 Torr;
13%
28%
4%
53%
In benzene; at 400 ℃; under 760 Torr;
16%
27%
4%
51%
endo-bicyclo<2.2.1>heptane-2-thiol

endo-bicyclo<2.2.1>heptane-2-thiol

norbornene
498-66-8

norbornene

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

tricyclo<2.2.1.0<sup>2,6</sup>>heptane
279-19-6

tricyclo<2.2.1.02,6>heptane

norbornane
279-23-2

norbornane

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

Conditions
Conditions Yield
In benzene; at 400 ℃; under 760 Torr; Product distribution; Mechanism; study of the pyrolysis of bicyclo<2.2.1>heptane-2-thiols; also other reaction conditions;
51%
16%
27%
2%
4%
(1α,4α,4aα,5α,8α,8aα)-1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene
1076-13-7

(1α,4α,4aα,5α,8α,8aα)-1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

endo-pentacylo<6.4.0.0<sup>2,10</sup>.0<sup>3,7</sup>.0<sup>9,11</sup>>dodec-4-ene

endo-pentacylo<6.4.0.02,10.03,7.09,11>dodec-4-ene

Conditions
Conditions Yield
at 275 ℃; Product distribution; Mechanism;
69%
C<sub>29</sub>H<sub>28</sub>O
116417-06-2

C29H28O

4,7-dimethyl-5,6-diphenylisobenzofuran
61051-07-8

4,7-dimethyl-5,6-diphenylisobenzofuran

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

(1S,6R)-2,5-Dimethyl-3,4-diphenyl-8-oxa-tricyclo[4.3.2.0<sup>1,6</sup>]undeca-2,4,10-triene
116417-07-3

(1S,6R)-2,5-Dimethyl-3,4-diphenyl-8-oxa-tricyclo[4.3.2.01,6]undeca-2,4,10-triene

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

Conditions
Conditions Yield
flash vacuum pyrolysis (F. V. P.);
exo-endo-tetracyclo[4.4.1<sup>2,5</sup>.1<sup>7,10</sup>.0<sup>1,6</sup>]dodeca-3,8-diene
15914-94-0

exo-endo-tetracyclo[4.4.12,5.17,10.01,6]dodeca-3,8-diene

cyclopenta-1,3-diene
542-92-7,25568-84-7,7313-32-8

cyclopenta-1,3-diene

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
Conditions Yield
In various solvent(s); at 160 ℃; Product distribution; Kinetics; Thermodynamic data; further temperatures; ΔH(excit.), ΔS(excit.);

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