- METHOD FOR PRODUCING CYCLODODECANONE
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The invention relates to a method for producing cyclododecanone by reacting cyclododecen with dinitrogen, especially a method comprising steps (I) and (II): (I) producing cyclododecen by partially hydrating cyclododecatriene; (II) reacting the cyclododecen obtained in step (I) with dinitrogen monoxide, thereby obtaining cyclododecanone.
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Page/Page column 27-28
(2008/06/13)
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- Reaction of arylsulfonylhydrazones of aldehydes with α-magnesio sulfones. A novel olefin synthesis
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Reactions of representative tosylhydrazones of aldehydes and ketones with α-metalated sulfones were examined in order to develop a practical olefination method. Treatment of aldehyde tosylhydrazone 2 with an excess of α-lithiated methyl phenyl or dimethyl sulfones yielded 3a. The reaction of 2 with sterically unhindered lithiated alkyl sulfones gave mixtures of the respective olefination products 3b-d along with the Shapiro fragmentation product 4. Sterically hindered lithiated sulfones afforded Shapiro products exclusively. In contrast, aldehyde tosylhydrazones 2 or 6 in reactions with a variety of α-magnesio primary or secondary alkyl sulfones gave olefination products 3a-j and 7a-c in high yields (Tables 1 and 2). β-Branched alkyl sulfones afforded predominantly (E)-alkenes, whereas unhindered primary sulfones gave mixtures of (E)- and (Z)- alkenes with low selectivity. Reaction of the 2,4,6-triisopropylbenzenesulfonylhydrazone (trisylhydrazone) of cyclodecanone 11c with α-magnesio methyl phenyl sulfone afforded the methylidene derivative 12a contaminated with the Shapiro product 13. Tosylhydrazone 2 resisted reaction with i-PrMgCl and gave only a small amount of the addition product in reaction with Bu2Mg. Some mechanistic aspects of the reaction of tosylhydrazones with organomagnesium compounds are discussed.
- Kurek-Tyrlik,Marczak,Michalak,Wicha,Zarecki
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p. 6994 - 7001
(2007/10/03)
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- Solvent-free, low-temperature, selective hydrogenation of polyenes using a bimetallic nanoparticle Ru-Sn catalyst
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The point of attachment of bimetallic Ru6Sn particles which are anchored to the pore walls of a highly dispersed high-area mesoporous silica is found to be the tin atom, as indicated by in situ and ex situ measurements. This catalyst displays high activity for the low-temperature, selective hydrogenation of cyclic polyenes under solvent-free conditions (see scheme).
- Hermans, Sophie,Raja, Robert,Thomas, John M.,Johnson, Brian F. G.,Sankar, Gopinathan,Gleeson, David
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p. 1211 - 1215
(2007/10/03)
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- A Convenient and High Yielding Procedure for the Preparation of Isoselenocyanates. Synthesis and Reactivity of O-Alkylselenocarbamates.
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A high yielding one pot procedure for the preparation of isoselenocyanate from the corresponding formamide is reported.Various aromatic and aliphatic primary amines were employed in order to prepare the isoselenocyanates to establish the generality of the procedure.O-Alkylselenocarbamates of various primary, secondary and tertiary alcohols were synthesized and their stability and comparative reactivity were studied.Radical deoxygenation of the selenocarbamate of a secondary and a tertiary alcohol was accomplished under various conditions.
- Barton, Derek H. R.,Parekh, Shyamal I.,Tajbakhsh, Mahmoud,Theodorakis, Emmanouil A.,Tse, Chi-Lam
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p. 639 - 654
(2007/10/02)
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- Synthesis of a Titaniumsilicoaluminate Isomorphous to Zeolite Beta and its Application as a Catalyst for the Selective Oxidation of Large Organic Molecules
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The isomorphous substitution of Si by Ti in the zeolite Beta framework by direct hydrothermal synthesis gives rise to useful catalysts for the selective oxidation of small and large organic compounds.
- Camblor, Miguel A.,Corma, Avelino,Martinez, Agustin,Perez-Parmente, Joaquin
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p. 589 - 590
(2007/10/02)
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- New Desulfurizations by Nickel-Containing Complex Reducing Agents
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Desulfurizations of saturated aliphatic or aromatic sulfoxides or sulfones are efficiently performed with nickel complex reducing agents (NiCRA's).The complete desulfurization of dithioketals can be effected in high yields with these reagents, while their half-desulfurization is efficiently achieved with 2,2'-bipyridine-modified nickel complex reducing agents (NiCRA-bpy).The desulfurization of vinyl thioethers, sulfoxides, and sulfones have been shown to be chemoselective, leaving the C-C double bond intact.The desulfurization of (E)-PhSO2(CH3)C=CHPh to cis-CH3CH=CHPh with NiCRA in the presence of quinoline is 95percent enantioselective.
- Becker, Sandrine,Fort, Yves,Caubere, Paul
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p. 6194 - 6198
(2007/10/02)
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- β'β ANIONIC ELIMINATION OF CARBOXYLIC ESTERS
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The elimination of lithium, magnesium and aluminium enolates of isobutyrates of medium ring cyclanols occurs in a syn fashion.A set of experimental procedures is presented.This elimination seems to be restricted to strained systems.The stereochemistry has been determined on stereospecifically deuterated cyclooctanol isobutyrates.The primary isotope effect kH/k2 was 3.0 +/- 0.1 and the secondary 1.1.The name β'β elimination is proposed for this syn elimination and related elimination.
- Aubert, Corinne,Begue, Jean-Pierre,Biellmann, Jean-Francois
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p. 5581 - 5590
(2007/10/02)
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- Double Bond Geometry of the Alkenes produced by Oxidative Elimination of Alkyl Phenyl Selenides and Tellurides
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Treatment of secondary-alkyl phenyl selenides with various oxidants affords the corresponding trans-alkene highly selectively irrespective of the amount of oxidant, while in the case of the tellurium analogues the double bond geometry of the product alkene depends markedly on the amount of oxidant, the trans-isomer being formed highly selectively with 1 equiv. oxidant and the proportion of the cis-isomer being increased with excess (2-10 equiv.) of oxidant.
- Uemura, Sakae,Hirai, Yasuyuki,Ohe, Kouichi,Sugita, Nobuyuki
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p. 1037 - 1038
(2007/10/02)
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- Stereospecific trans-elimination of 2-alkoxy- and 2-cycloalkoxytropones to alkenes and cycloalkenes
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The title compounds undergo thermal fragmentation to tropolones and alkenes and cycloalkenes.Product distribution and kinetic analyses of specifically labelled deuterio compounds establish the process to be a concerted electrocyclic reaction.
- Takeshita, Hitoshi,Mametsuka, Hiroaki
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p. 2035 - 2040
(2007/10/02)
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- REACTION OF BROMOHYDRINS WITH CHLOROTRIS(TRIPHENYLPHOSPHINE)COBALT(I)
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Bromohydrins were converted into ketones in high yields by the reaction with chlorotris(triphenylphosphine)cobalt(I) in the presence of amine or olefin.A probable path-way for the formation of ketones from bromohydrins was also described.
- Momose, Den-ichi,Yamada, Yasuji
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p. 2669 - 2672
(2007/10/02)
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