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Discovery of a Neutral 40-PdII-Oxo Molecular Disk, [Pd40O24(OH)16{(CH3)2AsO2}16]: Synthesis, Structural Characterization, and Catalytic Studies
We report on the synthesis and structural characterization of a giant, discrete, and neutral molecular disk, [Pd40O24(OH)16{(CH3)2AsO2}16] (Pd40), comprising a 40-palladium-oxo core that is capped by 16 dimethylarsinate moieties, resulting in a palladium-oxo cluster (POC) with a diameter of μ2 nm. Pd40, which is the largest known neutral Pd-based oxo cluster, can be isolated either as a discrete species or constituting a 3D H-bonded organic-inorganic framework (HOIF) with a 12-tungstate Keggin ion, [SiW12O40]4- or [GeW12O40]4-. 1H and 13C NMR as well as 1H-DOSY NMR studies indicate that Pd40 is stable in aqueous solution, which is also confirmed by ESI-MS studies. Pd40 was also immobilized on a mesoporous support (SBA15) followed by the generation of size-controlled Pd nanoparticles (diameter μ2-6 nm, as based on HR-TEM), leading to an effective heterogeneous hydrogenation catalyst for the transformation of various arenes to saturated carbocycles.
Bhattacharya, Saurav,Bons, Anton-Jan,Cadot, Emmanuel,Espenship, Michael Forrester,Haouas, Mohamed,Jaensch, Helge,Kortz, Ulrich,Laskin, Julia,Ma, Xiang,Mougharbel, Ali S.,Stuerzer, Tobias,Su, Pei,Taffa, Dereje H.,Wark, Michael
p. 17339 - 17347
(2021/11/17)

Polysilane-Immobilized Rh-Pt Bimetallic Nanoparticles as Powerful Arene Hydrogenation Catalysts: Synthesis, Reactions under Batch and Flow Conditions and Reaction Mechanism
Hydrogenation of arenes is an important reaction not only for hydrogen storage and transport but also for the synthesis of functional molecules such as pharmaceuticals and biologically active compounds. Here, we describe the development of heterogeneous Rh-Pt bimetallic nanoparticle catalysts for the hydrogenation of arenes with inexpensive polysilane as support. The catalysts could be used in both batch and continuous-flow systems with high performance under mild conditions and showed wide substrate generality. In the continuous-flow system, the product could be obtained by simply passing the substrate and 1 atm H2 through a column packed with the catalyst. Remarkably, much higher catalytic performance was observed in the flow system than in the batch system, and extremely strong durability under continuous-flow conditions was demonstrated (>50 days continuous run; turnover number >3.4 × 105). Furthermore, details of the reaction mechanisms and the origin of different kinetics in batch and flow were studied, and the obtained knowledge was applied to develop completely selective arene hydrogenation of compounds containing two aromatic rings toward the synthesis of an active pharmaceutical ingredient.
Miyamura, Hiroyuki,Suzuki, Aya,Yasukawa, Tomohiro,Kobayashi, Shu
supporting information
p. 11325 - 11334
(2018/09/06)

A new approach for the preparation of well-defined Rh and Pt nanoparticles stabilized by phosphine-functionalized silica for selective hydrogenation reactions
In this work, a new methodology for the synthesis of well-defined metallic nanoparticles supported on silica is described. This methodology is based on the surface control provided by SOMC. The nanoparticles are formed via the organometallic approach and are catalytically active in the hydrogenation of p-xylene, 3-hexyne, 4-phenyl-2 butanone, benzaldehyde, and furfural.
Llop Castelbou,Szeto,Barakat,Merle,Godard,Taoufik,Claver
supporting information
p. 3261 - 3264
(2017/03/20)

METHODS FOR SELECTIVELY HYDROGENATING SUBSTITUTED ARENES WITH SUPPORTED ORGANOMETALLIC CATALYSTS
Methods for selectively hydrogenating substituted arenes with a supported organometallic hydrogenating catalyst are provided. An exemplary method includes contacting a substituted arene-containing reaction stream with hydrogen in the presence of a supported organometallic hydrogenating catalyst under reaction conditions effective to selectively hydrogenate the substituted arenes to the cis isomer with high selectivity. In this method, the supported organometallic hydrogenating catalyst includes a catalytically active organometallic species and a Br?nsted acidic sulfated metal oxide support.
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(2016/06/28)

Nanoheterogeneous ruthenium-containing catalysts based on dendrimers in the hydrogenation of aromatic compounds under two-phase conditions
Nanoheterogeneous catalysts based on ruthenium nanoparticles dispersed in crosslinked dendrimer matrixes with a size of polymer particles of 100–500 nm show high activity in the hydrogenation of aromatic compounds under two-phase conditions. The addition of water to the reaction medium exerts a strong promoting effect on the activity of the catalysts: The turnover frequency increases by a factor of 3–90 depending on the substrate. When bimetallic (PdRu) nanoparticles are incorporated into the catalyst composition, the rate of benzene hydrogenation increases while the rate of transformation of substituted benzenes decreases.
Karakhanov,Maximov,Zolotukhina,Terenina,Vutolkina
p. 491 - 502
(2016/07/29)

Single-Face/All-cis Arene Hydrogenation by a Supported Single-Site d0 Organozirconium Catalyst
The single-site supported organozirconium catalyst Cp?ZrBz2/ZrS (Cp?=Me5C5, Bz=benzyl, ZrS=sulfated zirconia) catalyzes the single-face/all-cis hydrogenation of a large series of alkylated and fused arene derivatives to the corresponding all-cis-cyclohexanes. Kinetic/mechanistic and DFT analysis argue that stereoselection involves rapid, sequential H2 delivery to a single catalyst-bound arene face, versus any competing intramolecular arene π-face interchange. Stereocontrol is on: A single-site supported organozirconium catalyst exhibits unprecedented all-cis stereo/face-selective hydrogenation of substituted alkylarenes under mild reaction conditions. The resulting stereopure cycloalkanes offer new building blocks for value-added fine chemicals.
Stalzer, Madelyn Marie,Nicholas, Christopher P.,Bhattacharyya, Alak,Motta, Alessandro,Delferro, Massimiliano,Marks, Tobin J.
p. 5263 - 5267
(2016/04/26)

Hydrogenation of arenes, nitroarenes, and alkenes catalyzed by rhodium nanoparticles supported on natural nanozeolite clinoptilolite
Abstract Nanozeolite clinoptilolite supported rhodium nanoparticles (Rh/NZ-CP) has been prepared and characterized by a variety of techniques, including XRD, BET, TEM, EDX, ICP-OES and XPS analysis. This nanomaterial contains 2 wt% Rh in the range of 5-20 nm metallic nanoparticles distributed on nanozeolite. The catalytic performance of Rh/NZ-CP was evaluated by the hydrogenation of arenes, nitroarenes, and alkenes under moderate reaction conditions. The prepared nanocatalyst can be facilely recovered and reused many times without significant decrease in activity and selectivity. The high catalytic activity, thermal stability and reusability, simple recovery and eco-friendly nature make present catalyst as a unique catalytic system, which is particularly attractive in green chemistry.
Baghbanian, Seyed Meysam,Farhang, Maryam,Vahdat, Seyed Mohammad,Tajbakhsh, Mahmood
p. 128 - 136
(2015/07/15)

A mild route to solid-supported rhodium nanoparticle catalysts and their application to the selective hydrogenation reaction of substituted arenes
A clean route is described for the preparation of 1.3% (w/w) supported rhodium nanoparticle (3.0 ± 0.7 nm) catalysts onto commercial ion-exchange resins. Their application to the liquid-phase hydrogenation reaction of C=C bonds shows the most active species are obtained under catalytic conditions at room temperature and 1 bar H2. The heterogeneous catalyst shows excellent activity, selectivity and reusability in the hydrogenation reaction of alkenes and substituted arenes under very undemanding conditions. The results are discussed in terms of support effect on the catalytic efficiency.
Moreno-Marrodan, Carmen,Liguori, Francesca,Mercadé, Elisabet,Godard, Cyril,Claver, Carmen,Barbaro, Pierluigi
p. 3762 - 3772
(2015/07/01)

Ligand effect in the Rh-NP catalysed partial hydrogenation of substituted arenes
The Rh nanoparticles Rh1-Rh4 stabilised by the mono- and bidentate phosphine and phosphite ligands I-IV were synthesised, characterised and applied as catalysts in the partial hydrogenation of substituted arenes. In the case of disubstituted arenes, selectivities for the corresponding cyclohexene derivatives of up to 39% were achieved at ca. 40% conversion. The effect of parameters such as temperature and pressure was also examined. In the hydrogenation of styrene, very high selectivities for ethylbenzene were achieved with TOF values up to ca. 23500 h-1. All these results show that the catalytic performance of small Rh-NPs can be modulated by the appropriate choice of stabilising agents.
Castelbou, Jessica Llop,Gual, Aitor,Mercade, Elisabet,Claver, Carmen,Godard, Cyril
p. 2828 - 2833
(2013/09/24)

Moving from surfactant-stabilized aqueous rhodium (0) colloidal suspension to heterogeneous magnetite-supported rhodium nanocatalysts: Synthesis, characterization and catalytic performance in hydrogenation reactions
Wet impregnation of pre-synthesized surfactant-stabilized aqueous rhodium (0) colloidal suspension on silica was employed in order to prepare supported Rh0 nanoparticles of well-defined composition, morphology and size. A magnetic core-shell support of silica (Fe3O4@SiO 2) was used to increase the handling properties of the obtained nanoheterogeneous catalyst. The nanocomposite catalyst Fe3O 4@SiO2-Rh0 NPs was highly active in the solventless hydrogenation of model olefins and aromatic substrates under mild conditions with turnover frequencies up to 143,000 h-1. The catalyst was characterized by various transmission electron microscopy techniques showing well-dispersed rhodium nanoparticles (～3 nm) mainly located at the periphery of the silica coating. The heterogeneous magnetite-supported nanocatalyst was investigated in the hydrogenation of cyclohexene and compared to the previous surfactant-stabilized aqueous Rh0 colloidal suspension and various silica-supported Rh0 nanoparticles. Finally, the composite catalyst could be reused in several runs after magnetic separation.
Pélisson, Carl-Hugo,Vono, Lucas L.R.,Hubert, Claudie,Denicourt-Nowicki, Audrey,Rossi, Liane M.,Roucoux, Alain
experimental part
p. 124 - 129
(2012/06/18)

Chemically modified cyclodextrins as supramolecular tools to generate carbon-supported ruthenium nanoparticles: An application towards gas phase hydrogenation
A series of carbon-supported ruthenium catalysts was synthesized from zerovalent ruthenium nanoparticles stabilized by randomly methylated cyclodextrins (α-, β- and γ-CD) followed by their adsorption onto the carbon support. The catalysts were characterized by N2 physisorption and thermal analyses. The deposited ruthenium nanoparticles were characterized by transmission electron microscopy, which has highlighted predominantly spherical shapes with a mean diameter of 2.4 nm. Catalytic activity was investigated in the gas phase hydrogenation of o-, m- and p-xylene at 85 °C, both separately and in a two-component mixture (o- and p-xylene). The catalyst prepared by a 1:3 concentration ratio of RuCl3 to randomly methylated β-cyclodextrin exhibited the highest hydrogenation activity and stereoselectivity toward the formation of trans- dimethylcyclohexane. The β-cyclodextrin appeared as multifunctional molecular receptors enabling the stabilization and dispersion of the metallic nanoparticles onto the support and the promotion of the catalytic reaction through host-guest interactions.
Wyrwalski,Léger,Lancelot,Roucoux,Monflier,Ponchel
experimental part
p. 334 - 341
(2011/10/02)

Polyhydroxylated ammonium chloride salt: A new efficient surfactant for nanoparticles stabilisation in aqueous media. Characterization and application in catalysis
A trihydroxyammonium chloride has proved to be an efficient protective agent for Rh(0) nanoparticles and the hydrogenation of arene compounds has been investigated. Significant formation of cyclohexanone in the reduction of anisole has been demonstrated. The Royal Society of Chemistry 2009.
Hubert, Claudie,Denicourt-Nowicki, Audrey,Guegan, Jean-Paul,Roucoux, Alain
experimental part
p. 7356 - 7358
(2010/01/06)

Rhodium nanoparticles entrapped in boehmite nanofibers: Recyclable catalyst for arene hydrogenation under mild conditions
A new recyclable rhodium catalyst was synthesized by a simple procedure from readily available reagents, which showed high activities in the hydrogenation of various arenes under 1 atm H2 at room temperature. The Royal Society of Chemistry 2005.
Park, In Soo,Kwon, Min Serk,Kim, Namdu,Lee, Jae Sung,Kang, Kyung Yeon,Park, Jaiwook
p. 5667 - 5669
(2007/10/03)

Surfactant-stabilized aqueous iridium(0) colloidal suspension: An efficient reusable catalyst for hydrogenation of arenes in biphasic media
Aqueous suspensions of iridium nanoparticles produced by the chemical reduction of IrCl3 assisted by sonication, in the presence of N,N-dimethyl-N-cetyl-N-(2-hydroxyethyl)ammonium chloride salt as surfactant, have shown an efficient activity for the catalytic hydrogenation of various aromatic derivatives in biphasic media under mild conditions. These nanocatalysts can be reused for further runs with a total conservation of activity and provided significant catalytic lifetime for anisole hydrogenation in pure water with 3000 total turnover (TTO).
Mevellec, Vincent,Roucoux, Alain,Ramirez, Esther,Philippot, Karine,Chaudret, Bruno
p. 72 - 76
(2007/10/03)

Arene Hydrogenation with a Stabilised Aqueous Rhodium(0) Suspension: A Major Effect of the Surfactant Counter-Anion
A reduced aqueous colloidal suspension of rhodium shows an efficient activity in the catalytic hydrogenation of various benzene derivatives under biphasic conditions at room temperature and under atmospheric hydrogen pressure. The rhodium nanoparticles in the size range of 2-2.5 nm have been synthesised by reducing RhCl3 · 3 H2O with sodium borohydride and were stabilised by highly water-soluble N,N-dimethyl-N-cetyl-N-(2- hydroxyethyl)ammonium salts (HEA16X, X = Br, Cl, I, CH3SO 3, BF4). The major influence of the counter-ion of these surfactants on catalytic activity and recycling is described. The best results have been obtained with chloride ammonium salts HEA16Cl.
Roucoux, Alain,Schulz, Jürgen,Patin, Henri
p. 222 - 229
(2007/10/03)

Catalytic hydrogenation of aromatics under biphasic conditions: Isolation and structural characterisation of the cluster intermediate [(η6-C6Me6)2(η 6-C6H6)Ru3(μ2-H) 2(μ2-OH)(μ3-O)]+
The water-soluble cluster cation [(η6-C6Me6)2(η 6-C6H6)Ru3(μ2-H) 3(μ3-O)]+ (2) catalyses the hydrogenation of benzene and benzene derivatives to give the corresponding cyclohexanes under biphasic conditions. The catalytic activity of 2 depends markedly on the substrate, an extremely high activity being observed for ethylbenzene. The cationic species present in the catalytic mixture of the ethylbenzene hydrogenation could be isolated as the tetrafluoroborate salt and characterised as the cation [(η6-C6Me6)2(η 6-C6H6)Ru3(μ2-H) 2(μ2-OH)(μ3-O)]+ (3). With 3 as the catalyst, the catalytic activity is also much higher for other benzene derivatives.
Faure, Matthieu,Vallina, Ana Tesouro,Stoeckli-Evans, Helen,Süss-Fink, Georg
p. 103 - 108
(2007/10/03)

Colloid-catalysed arene hydrogenation in aqueous/supercritical fluid biphasic media
Hydrogenation of arenes, including the lignin model compound 2-methoxy- 4-propylphenol, has been effected using a Rh colloid in biphasic aqueous/supercritical ethane reaction media; this is the first successful example of an unsupported colloid-catalysed hydrogenation of a substrate in a supercritical fluid; the same reaction does not proceed in aqueous/supercritical carbon dioxide or ionic liquid/supercritical fluid media.
Bonilla, R. Jason,James, Brian R.,Jessop, Philip G.
p. 941 - 942
(2007/10/03)

Stabilized rhodium(0) nanoparticles: A reusable hydrogenation catalyst for arene derivatives in a biphasic water-liquid system
A colloidal system based on an aqueous suspension of rhodium(0) nanoparticles proved to be an efficient catalyst for the hydrogenation of arene derivatives under biphasic conditions. The rhodium nanoparticles (2 - 2.5 nm) were synthesized by the reduction of RhCl3·3 H2O with sodium borohydride and were stabilized by highly water-soluble N-alkyl-N-(2- hydroxyethyl)ammonium salts (HEA-C(n)). These surfactant molecules were characterized by measurements of the surface tension and the aqueous dispersions with rhodium were observed by transmission electron cryomicroscopy. The catalytic system is efficient under ultramild conditions, namely room temperature and 1 atm H2 pressure. The aqueous phase which contains the protected rhodium(0) colloids can be reused without significant loss of activity. The microheterogeneous behavior of this catalytic system was confirmed on a mercury poisoning experiment.
Schulz, Juergen,Roucoux, Alain,Patin, Henri
p. 618 - 624
(2007/10/03)

Unprecedented efficient hydrogenation of arenes in biphasic liquid-liquid catalysis by re-usable aqueous colloidal suspensions of rhodium
A reduced aqueous colloidal suspension of rhodium shows efficient activity for the catalytic hydrogenation of various benzene derivatives under biphasic conditions at room temperature and under atmospheric hydrogen pressure; the aqueous phase containing the Rh(0) particles can be re-used for further runs with a complete conservation of activity.
Schulz, Juergen,Roucoux, Alain,Patin, Henri
p. 535 - 536
(2007/10/03)

Oxidation of 1,4-dimethylcyclohexane by perchloric acid catalyzed by polyphenylferrosiloxane
The reaction of oxidation of 1,4-dimethylcyclohexane (DMCH) by perchloric acid at ～20 °C catalyzed by polyphenylferrosiloxane has been found. The chromatographic analysis has revealed the formation of several products, including the tertiary alcohol with 100% retention of the configuration of the initial configuration. The specific feature of the process is the following: along with the high stereospecific formation of the tertiary alcohol, cis-trans isomerization in the starting 1,4-DMCH is observed. The data obtained are discussed on the basis of the mechanism, including the formation of a ferryl intermediate with the subsequent transfer of the oxygen atom to the tertiary C-H bond of 1,4-DMCH through the intermediate complex with the five-coordinated carbon.
Kulikova,Levitsky,Shestakov,Shilov
p. 435 - 437
(2007/10/03)

The hydrogenation of o-, m-, and p-xylene over Ni/SiO2
The gas phase hydrogenation of o-, m-, and p-xylene was studied over a Ni/SiO2 catalyst prepared by homogeneous precipita tion/deposition. The hydrogenation of each xylene yielded steroisomeric product mixtures of the saturated dimethylcyclohexane. The stereospecificity of the reaction is related to the nature of the reactant/catalyst interaction which governs the mode of addition of hydrogen to the carbons bearing the methyl substituents. The appearance of a common well-defined reversible maximum (Tmax) in the rate vs. temperature plots is reported and discussed. Reaction orders with respect to xylene partial pressures are plotted as a function of reaction temperature. The temperature dependence of the rate constants was fitted to an Arrhenius equation and generated positive (T ≤ Tmax) and negative (T ≥ Tmax) activation energies. The derivation of true activation energies and heats of adsorption from the kinetic data is presented. Turnover frequencies at a particular temperature decreased in the order p-xylene > m-xylene > o-xylene. The respective roles of steric and electronic effects in determining the strength of adsorption and surface reactivity are discussed. A compensation effect, which is established for the experimentally determined or apparent kinetic parameters, is attributed to variations in the temperature dependencies of the surface concentration of the reactive species.
Keane, Mark A.
p. 347 - 355
(2007/10/03)

MECHANISMS OF FREE-RADICAL REACTIONS. XVIII. STEREOSELECTIVITY OF THE TRANSFER OF A HYDROGEN ATOM DURING THE FREE-RADICAL REDUCTION OF SUBSTITUTED CYCLOHEXYL HALIDES
The stereochemistry of the free-radical reduction of cis- and trans-4-tert-butylcyclohexyl halides by trialkyldeuterostannanes R3SnD was studied.Irrespective of the nature of the halogen atom (bromine or chlorine) and the stereochemistry of the initial halide, the predominant reaction product is cis-4-deutero-tert-butylcyclohexane with axial orientation of the deuterium atom ( cca 80percent, 13C NMR).The stereoselectivity of the transfer of the deuterium atom to the 4-tert-butylcyclohexyl radical is determined by the torsial strain in the transition state.The reduction of 1,4-dimethylcyclohexyl chloride by the reagents R3EH (E=Sn, Ge) gives a mixture of trans(e,e)- and cis(e,a)-1,4-dimethylcyclohexanes richer in the trans isomer.
Dneprovskii, A. S.,Pertsikov, B. Z.,Chertkov, V. A.
p. 291 - 294
(2007/10/02)

CATALYTIC HYDROGENATION OF OLEFINS, ACETYLENES AND ARENES BY RHODIUM TRICHLORIDE AND ALIQUAT-336 UNDER PHASE TRANSFER CONDITIONS
The ion pair formed aqueous rhodium trichloride and aliquat-336 in dichloroethane catalyzes hydrogenation of a variety of unsaturated compounds.Aromatics are reduced to cyclohexane derivatives under exceedingly mild conditions.
Blum, Jochanan,Amer, Ibrahim,Zoran, Amikam,Sasson, Yoel
p. 4139 - 4142
(2007/10/02)

n-? Interaction between an Oxygen Lone Pair and ?-Electrons in Cyclic Allylic Alcohols and Ethers; Carbon-13 Nuclear Magnetic Resonance Spectra, Catalytic Hydrogenation, and CNDO/2 Calculations
In order to elucidate the n-? interaction between an oxygen lone pair and ?-electrons, 13C n.m.r. spectra have been obtained for several cyclic allylic alcohols and ethers.The chemical shifts for sp2-carbons of these compounds are compared with those of the corresponding hydrocarbons.The chemical shift differences (Δδ) between compounds in which the oxygen atoms are placed at an anticlinal position with respect to the double bond and the corresponding hydrocarbons are different from those of a set of compounds, the oxygens of which are synperiplanar.We have also studied catalytic hydrogenation of and CNDO/2 calculations for these cyclic allylic compounds.These results are discussed in terms of homoconjugation.
Ishiyama, Jun-ichi,Senda, Yasuhisa,Imaizumi, Shin
p. 71 - 76
(2007/10/02)

CATALYTIC ACTIVITY OF Pt/AlPO4 AND RELATED SYSTEMS. II. GAS PHASE HYDROGENATION OF XYLENES
In the present paper data are reported on the gas-phase hydrogenation of o-, m-, and p-xylene and o-, m-, p-ethylmethylbenzene using a pulse reactor.New systems obtained by supporting Pt on AlPO4-Al2O3 (75/25), pure AlPO4 and SiO4-AlPO4 (80/20) have been used as catalysts.The effect of the reduction temperature of the catalysts and the hydrogen pressure on the selectivity to cis- and trans-dimethylcyclohexanes and ethylmethylcyclohexanes has been investigated.The result obtained are interpreted by assuming a Horiuti-Polanyi mechanism, with suprafacial addition of hydrogen.
Aramendia, M. A.,Borau, V.,Jimenez, C.,Marinas, J. M.
p. 743 - 750
(2007/10/02)

HYDROGENOLYSIS OF HYDROCARBONS OVER SUPPORTED CATALYSTS DERIVED FROM METAL CARBONYL CLUSTERS
A comparison between the activities of silica-supported ruthenium, rhodium and platinum catalysts prepared from metal cluster compounds and their conventional analogues towards the activation of saturated hydrocarbons has been made.Ruthenium cluster-derived catalysts display greatly enhanced activity for the complete hydrogenolysis of straight chain aliphatic hydrocarbons to methane and provide a temperature advantage of 150 deg C relative to conventionally prepared ruthenium catalysts where only moderate hydrocarbon conversions are noted.The increased activity superficially correlates with the smaller metal crystallite sizes (15-20 Angstroem) reproducibly obtainable using metal cluster compounds as catalyst precursors.The highly specific activity for the hydrogenolysis of C-C bonds in saturated hydrocarbons has been applied to the selective cleavage of the alkyl group in ethylbenzene, giving toluene and methane.Conversions of up to 30percent ethylbenzene have been observed at 225 deg C and 1 atm using a Ru3(CO)12/SiO2- based catalyst.The xylenes, particularly o-xylene, are much less susceptible to hydrogenolysis and, at 225 deg C, relative hydrocarbon destruction rates of 30:1 and 7:1 have been observed using mixed feeds of ethylbenzene/o-xylene and ethylbenzene/p-xylene, respectively.Such a catalyst system can, in principle, therefore provide a means of separating ethylbenzene from its mixtures with xylenes.
Simpson, A. F.,Whyman, R.
p. 157 - 174
(2007/10/02)

Neue C8H10-Isomere: 2-Methylenbicyclohept-6-en und 3-Methylentricyclo2,7>heptan - thermische und metallkatalysierte Umlagerungen
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Hasselmann, Dieter,Loosen, Klaus
p. 651 - 652
(2007/10/02)