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RESEARCH PAPER · Angewandte Chemie International Edition · 2007

Reduction of Phenyl Silyl Acetylenes with Lithium: Unexpected Formation of a Dilithium Dibenzopentalenide

Masaichi Saito, Michio Nakamura, Tomoyuki Tajima, Michikazu Yoshioka

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Reduction of Phenyl Silyl Acetylenes with Lithium: Unexpected Formation of a Dilithium DibenzopentalenideOriginalRelapsing polychondritis: new pulmonary manifestations.9Formation of stable enols from 1,4-dilithio-1,3-dienes and acid chlorides by a de-aromatization/Michael addition/re-aromatization domino process11Tandem SiC and CH Activation for Decamethylhafnocene and Bis(trimethylsilyl)acetylene29Tandem‐Aktivierung von Si‐C‐ und C‐H‐Bindungen bei Decamethylhafnocen und Bis(trimethylsilyl)acetylen12Aromaticity of Group 14 Organometallics: Experimental Aspects200Aromatizität von metallorganischen Verbindungen mit Gruppe‐14‐Elementen: experimentelle Aspekte57Oxidation and Reduction0New Reactions of a Dibenzo[a,e]pentalene74(Z,Z)-1,4-Diiodo-1,4-bis(trimethylsilyl)buta-1,3-diene1Facile Carbolithiation of Bent Alkyne without Catalyst. Tandem Route to Dibenzo[b,f]pentalenes from Dibenzocyclooctadiyne64Novel Reactions of Steric Encumbered 1,4-Dilithio-1,3-butadiene with Group 14 Electrophiles: Formation and Structure of Stable Dihydroxygermole8An Extremely Simple Dibenzopentalene Synthesis from 2‐Bromo‐1‐ethynylbenzenes Using Nickel(0) Complexes: Construction of Its Derivatives with Various Functionalities126Intramolecular Reductive Double Cyclization of o,o′-Bis(arylcarbonyl)diphenylacetylenes: Synthesis of Ladder π-Conjugated Skeletons87Isolation, Structural Characterization, and Synthetic Application of Oxycyclopentadienyl Dianions42Isolation, Structural Characterization, and Synthetic Application of Oxycyclopentadienyl Dianions15Isolation and X-ray Structure of a Trimeric 1,4-Dilithio-1,3-butadiene and a Dimeric Me3Si-Substituted 1,4-Dilithio-1,3-butadiene40Pentaleno[1,2-c:4,5-c′]dithiophene Derivatives: First Synthesis, Properties, and a Molecular Structure51Synthesis and Reactions of Dibenzo[a,e]pentalenes1031,4-Dilithio-1,3-dienes: Reaction and Synthetic Applications131Dinaphthopentalenes: Pentalene Derivatives for Organic Thin‐Film Transistors196Dinaphthopentalenes: Pentalene Derivatives for Organic Thin‐Film Transistors701,4‐Diiodo‐1,3‐dienes: Versatile Reagents in Organic Synthesis29Synthesis of a Pentalene Centered Polycyclic Fused System45Development and Application of Polycyclic Conjugated Systems Bearing a Pentalene Skeleton1First structural evidence for multiple alkali metals between sandwich decks in a metallocene17Molecular Structure and Electronic State of the Dibenzo[a,e]pentalene Anion Radical22Gold‐Catalyzed Synthesis of Dibenzopentalenes – Evidence for Gold Vinylidenes275Organo-di-Lithio Reagents: Cooperative Effect and Synthetic Applications12Structural Perspective on Aggregation of Alkali Metal Ions with Charged Planar and Curved Carbon π-Surfaces45Unexpected Formation of Ru2Sn2 Bicyclic Four-Membered Ring Complexes with Butterfly and Inverse-Sandwich Structures24DFT Studies on the Reaction Mechanisms of 1,4-Dilithio 1,3-Dienes with Nitriles9Dibenzopentalenes from B(C6F5)3‐Induced Cyclization Reactions of 1,2‐Bis(phenylethynyl)benzenes114Dibenzopentalenes from B(C6F5)3‐Induced Cyclization Reactions of 1,2‐Bis(phenylethynyl)benzenes40Pd-Catalyzed Cascade Crossover Annulation of o-Alkynylarylhalides and Diarylacetylenes Leading to Dibenzo[a,e]pentalenes1033-D Brick-Wall Polymeric Structure of TMEDA-Supported 1,4-Dilithio-1,3-Butadiene9Barium Dibenzopentalenide as a Main‐Group Metal η8 Complex: Facile Synthesis from 1,4‐Dilithio‐1,3‐butadienes and Ba[N(SiMe3)2]2, Structural Characterization, and Reaction Chemistry52Barium Dibenzopentalenide as a Main‐Group Metal η8 Complex: Facile Synthesis from 1,4‐Dilithio‐1,3‐butadienes and Ba[N(SiMe3)2]2, Structural Characterization, and Reaction Chemistry19Pentalenes with novel topologies: exploiting the cascade carbopalladation reaction between alkynes and gem-dibromoolefins69Synthesis, Structure, and Reactivity of Lewis Base Stabilized Plumbacyclopentadienylidenes34Antiaromaticity in Nonbenzenoid Oligoarenes and Ladder Polymers13Functions Incorporating a Halogen and Another Group Other than a Halogen or a Chalcogen0Organometallic intermediate-based organic synthesis: organo-di-lithio reagents and beyond39The B(C6F5)3 Boron Lewis Acid Route to Arene‐Annulated Pentalenes41Facile Synthesis of Dibenzopentalene Dianions and Their Application as New π‐Extended Ligands19Enhancement of Stannylene Character in Stannole Dianion Equivalents Evidenced by NMR and Mössbauer Spectroscopy and Theoretical Studies of Newly Synthesized Silyl-Substituted Dilithiostannoles62Intramolecular C–F and C–H bond cleavage promoted by butadienyl heavy Grignard reagents60A reversible two-electron redox system involving a divalent lead species32Conversion of Zirconacyclopentadienes into Metalloles: Fagan–Nugent Reaction and Beyond127π‐Extended Pentalenes: The Revival of the Old Compound from New Standpoints57One-Shot Double Amination of Sondheimer–Wong Diynes: Synthesis of Photoluminescent Dinaphthopentalenes23Reaction of Dilithio Reagents with PhSiH 3 : Formation of Siloles and 3-Silacyclopentenes15Planar Cyclopenta‐Fused Polycyclic Arenes14Computational Studies on the Reaction from Silyl 1,4‐Dilithio 1,3‐butadiene to Lithio Silole1Calcium-Mediated C–H and C–F Bond Cleavage: Synthesis of Indenes and Perfluorodibenzopentalenes from 1,4-Dilithio-1,3-butadienes17Recent Developments in Fulvene and Heterofulvene Chemistry11Donor- and acceptor-functionalized dibenzo[a,e]pentalenes: modulation of the electronic band gap55Oxidation and Reduction0Selective synthesis of unsymmetric dibenzo[a,e]pentalenes by a rhodium-catalysed stitching reaction49Fast construction of dianthraceno[a,e]pentalenes for OPV applications18Facile Synthesis of Polycyclic Pentalenes with Enhanced Hückel Antiaromaticity99Facile Synthesis of Polycyclic Pentalenes with Enhanced Hückel Antiaromaticity31Reactions of Dilithium Dibenzopentalenides with Cr(CO)3(CH3CN)3: Unexpected Formation of a Cubic Tetramer of an Anionic Hydrodibenzopentalenyl Complex2Formation of Dibenzopentalene-linking Polymers under the Two-zone CVD and Wet Conditions7Synthesis and Structures of Sterically Encumbered Group 14 Monolithio Compounds and Unexpected Differences in Their Reactivity8Synthesis and Characterization of Dibenzo[a,f]pentalene: Harmonization of the Antiaromatic and Singlet Biradical Character99Dibenzo[a,e]pentalenes with Low-Lying LUMO Energy Levels as Potential n-Type Materials55Creation of Exotic π-Electron Systems by Introduction of Heavy Elements and Expansion of the Concept of Aromaticity18Antiaromatic character of cycloheptatriene-bis-annelated indenofluorene framework mainly originated from heptafulvene segment56Enhancement of Antiaromatic Character via Additional Benzoannulation into Dibenzo[a,f]pentalene: Syntheses and Properties of Benzo[a]naphtho[2,1-f]pentalene and Dinaphtho[2,1-a,f]pentalene78Synthesis of organometallic pentalenide complexes11Electronic Push–Pull Modulation by Peripheral Substituents in Pentaaryl Boroles23Diborative Reduction of Alkynes to 1,2-Diboryl-1,2-Dimetalloalkanes: Its Application for the Synthesis of Diverse 1,2-Bis(boronate)s51Iron(III)-Mediated Bicyclization of 1,2-Allenyl Aryl Ketones: Assembly of Indanone-Fused Polycyclic Scaffolds and Dibenzo[a,e]pentalene Derivatives182,5-Bis-trimethylsilyl substituted boroles20Recent Progress in High Linearly Fused Polycyclic Conjugated Hydrocarbons (PCHs, n > 6) with Well‐Defined Structures121Sodium-Metal-Promoted Reductive 1,2- syn -Diboration of Alkynes with Reduction-Resistant Trimethoxyborane38Breathing New Life into Nonalternant Hydrocarbon Chemistry: Syntheses and Properties of Polycyclic Hydrocarbons Containing Azulene, Pentalene, and Heptalene Frameworks167Dithieno[a,e]pentalenes: Highly Antiaromatic Yet Stable π‐Electron Systems without Bulky Substituents44Aromatic Metamorphosis of Thiophenes by Means of Desulfurative Dilithiation34Multiplex antibacterial processes and risk in resistant phenotype by high oxidation-state nanoparticles: New killing process and mechanism investigations23Cations and Anions of Dibenzo[a,e]pentalene and Reduction of a Dibenzo[a,e]pentalenophane23Borole-based half-sandwich complexes of germanium and tin11Direct dilithiation of N-aryl heterocycles for the construction of condensed N-heterocycles2Expanding the series of alkali metal plumbolyl complexes to Na and K6Organometallic Complexes of the Alkali Metals6Assessing an Elusive 3,4‐Dimethyl‐Chloroborole3Holey penta-hexagonal graphene: a promising anode material for Li-ion batteries11Flash Communication: Nickel-Mediated Cyclotetramerization of Phenylacetylene to 1,2-Dihydropentalenylnickel Complex1Synthesis of a dilithiobutadiene bearing extremely bulky silyl substituents and its reactivity toward functionalized silanes2The interplay of antiaromaticity and diradical character in diarenoindacenes and diindenoarenes15Synthesis of Dibenzopentalenes via Pd(0)-Catalyzed Cascade Coupling of gem-Dibromo Olefins5Gram-Scale Synthesis of Dibenzo[ a , e ]pentalenes from Trialkyl(phenylethynyl)silanes via Organosodium Intermediates3Holey Penta-Hexagonal Graphene as an Anode in High-Efficiency Sodium-Ion Batteries5Lithium-mediated mechanochemical annulative dimerization of diarylacetylenes for synthesis of 1,4-dihydrodinaphthopentalenes1Modular synthesis of benzothiophene-fused pentalenes reveals substituent-dependent antiaromaticity2Streamlined synthesis of functionalized dibenzo[ a , e ]pentalenes through potassium-mediated cyclization and late-stage thianthrenation0

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  1. Relapsing polychondritis: new pulmonary manifestations.

    PubMed · 1992-02-01

    B P Burlew, H Lippton, D Klinestiver, E J Haponik

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  2. Formation of stable enols from 1,4-dilithio-1,3-dienes and acid chlorides by a de-aromatization/Michael addition/re-aromatization domino process

    Organic & Biomolecular Chemistry · 2007-01-01

    Qiaoshu Hu, Chao Wang, Dongzhen Li, Zhenfeng Xi

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  3. Tandem SiC and CH Activation for Decamethylhafnocene and Bis(trimethylsilyl)acetylene

    Angewandte Chemie International Edition · 2007-07-06

    Torsten Beweries, V.V. Burlakov, Marc A. Bach, Stephan Peitz, Perdita Arndt, Wolfgang Baumann, Anke Spannenberg, Uwe Rosenthal, Biswarup Pathak, Eluvathingal D. Jemmis

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  4. Tandem‐Aktivierung von Si‐C‐ und C‐H‐Bindungen bei Decamethylhafnocen und Bis(trimethylsilyl)acetylen

    Angewandte Chemie · 2007-07-06

    Torsten Beweries, V.V. Burlakov, Marc A. Bach, Stephan Peitz, Perdita Arndt, Wolfgang Baumann, Anke Spannenberg, Uwe Rosenthal, Biswarup Pathak, Eluvathingal D. Jemmis

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  5. Aromaticity of Group 14 Organometallics: Experimental Aspects

    Angewandte Chemie International Edition · 2007-08-02

    Vladimir Ya. Lee, Akira Sekiguchi

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  6. Aromatizität von metallorganischen Verbindungen mit Gruppe‐14‐Elementen: experimentelle Aspekte

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  7. Oxidation and Reduction

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  8. New Reactions of a Dibenzo[a,e]pentalene

    Chemistry - A European Journal · 2008-06-09

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  9. (Z,Z)-1,4-Diiodo-1,4-bis(trimethylsilyl)buta-1,3-diene

    Acta Crystallographica Section E Structure Reports Online · 2008-10-31

    Jan W. Bats, Birgit Urschel, Thomas Müller

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  10. Facile Carbolithiation of Bent Alkyne without Catalyst. Tandem Route to Dibenzo[b,f]pentalenes from Dibenzocyclooctadiyne

    Chemistry Letters · 2008-12-01

    Govindarajulu Babu, Akihiro Orita, Junzo Otera

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  11. Novel Reactions of Steric Encumbered 1,4-Dilithio-1,3-butadiene with Group 14 Electrophiles: Formation and Structure of Stable Dihydroxygermole

    Heterocycles · 2009-01-01

    Masaichi Saito, Michio Nakamura, Tomoyuki Tajima

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  12. An Extremely Simple Dibenzopentalene Synthesis from 2‐Bromo‐1‐ethynylbenzenes Using Nickel(0) Complexes: Construction of Its Derivatives with Various Functionalities

    Chemistry - A European Journal · 2009-02-02

    Takeshi Kawase, Akihito Konishi, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, Takashi Kubo

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  13. Intramolecular Reductive Double Cyclization of o,o′-Bis(arylcarbonyl)diphenylacetylenes: Synthesis of Ladder π-Conjugated Skeletons

    Organic Letters · 2009-06-18

    Hongyu Zhang, Takashi Karasawa, Hiroshi Yamada, Atsushi Wakamiya, Shigehiro Yamaguchi

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  14. Isolation, Structural Characterization, and Synthetic Application of Oxycyclopentadienyl Dianions

    Angewandte Chemie International Edition · 2009-09-22

    Lantao Liu, Wen‐Xiong Zhang, Chao Wang, Congyang Wang, Zhenfeng Xi

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  15. Isolation, Structural Characterization, and Synthetic Application of Oxycyclopentadienyl Dianions

    Angewandte Chemie · 2009-09-22

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  16. Isolation and X-ray Structure of a Trimeric 1,4-Dilithio-1,3-butadiene and a Dimeric Me3Si-Substituted 1,4-Dilithio-1,3-butadiene

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    Lantao Liu, Wen‐Xiong Zhang, Qian Luo, Heng Li, Zhenfeng Xi

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  17. Pentaleno[1,2-c:4,5-c′]dithiophene Derivatives: First Synthesis, Properties, and a Molecular Structure

    Chemistry Letters · 2010-02-20

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  18. Synthesis and Reactions of Dibenzo[a,e]pentalenes

    Symmetry · 2010-04-21

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  19. 1,4-Dilithio-1,3-dienes: Reaction and Synthetic Applications

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  20. Dinaphthopentalenes: Pentalene Derivatives for Organic Thin‐Film Transistors

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  21. Dinaphthopentalenes: Pentalene Derivatives for Organic Thin‐Film Transistors

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  22. 1,4‐Diiodo‐1,3‐dienes: Versatile Reagents in Organic Synthesis

    Chemistry - An Asian Journal · 2010-09-17

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  23. Synthesis of a Pentalene Centered Polycyclic Fused System

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    Xiaodong Yin, Yongjun Li, Yongjun Li, Yulan Zhu, Yu‐He Kan, Yuliang Li, Yuliang Li, Daoben Zhu

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  24. Development and Application of Polycyclic Conjugated Systems Bearing a Pentalene Skeleton

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  25. First structural evidence for multiple alkali metals between sandwich decks in a metallocene

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    Matthew S. Jeletic, Frédéric A. Perras, Serge I. Gorelsky, Jennifer J. Le Roy, Ilia Korobkov, David L. Bryce, Muralee Murugesu

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  26. Molecular Structure and Electronic State of the Dibenzo[a,e]pentalene Anion Radical

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  27. Gold‐Catalyzed Synthesis of Dibenzopentalenes – Evidence for Gold Vinylidenes

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  28. Organo-di-Lithio Reagents: Cooperative Effect and Synthetic Applications

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  29. Structural Perspective on Aggregation of Alkali Metal Ions with Charged Planar and Curved Carbon π-Surfaces

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  30. Unexpected Formation of Ru2Sn2 Bicyclic Four-Membered Ring Complexes with Butterfly and Inverse-Sandwich Structures

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  31. DFT Studies on the Reaction Mechanisms of 1,4-Dilithio 1,3-Dienes with Nitriles

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    Fei Zhao, Ming Zhan, Wen‐Xiong Zhang, Zhenfeng Xi

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  32. Dibenzopentalenes from B(C6F5)3‐Induced Cyclization Reactions of 1,2‐Bis(phenylethynyl)benzenes

    Angewandte Chemie International Edition · 2013-05-06

    Chao Chen, Marcel Harhausen, René Liedtke, Kathrin Bussmann, Aiko Fukazawa, Shigehiro Yamaguchi, Jeffrey L. Petersen, Constantin Gabriel Daniliuc, Roland Fröhlich, Gerald Kehr, Gerhard Erker

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  33. Dibenzopentalenes from B(C6F5)3‐Induced Cyclization Reactions of 1,2‐Bis(phenylethynyl)benzenes

    Angewandte Chemie · 2013-05-06

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  34. Pd-Catalyzed Cascade Crossover Annulation of o-Alkynylarylhalides and Diarylacetylenes Leading to Dibenzo[a,e]pentalenes

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    Jian Zhao, Kazuaki Oniwa, Naoki Asao, Yoshinori Yamamoto, Tienan Jin

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  35. 3-D Brick-Wall Polymeric Structure of TMEDA-Supported 1,4-Dilithio-1,3-Butadiene

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    Shaoguang Zhang, Ming Zhan, Wen‐Xiong Zhang, Zhenfeng Xi

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  36. Barium Dibenzopentalenide as a Main‐Group Metal η8 Complex: Facile Synthesis from 1,4‐Dilithio‐1,3‐butadienes and Ba[N(SiMe3)2]2, Structural Characterization, and Reaction Chemistry

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  37. Barium Dibenzopentalenide as a Main‐Group Metal η8 Complex: Facile Synthesis from 1,4‐Dilithio‐1,3‐butadienes and Ba[N(SiMe3)2]2, Structural Characterization, and Reaction Chemistry

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  38. Pentalenes with novel topologies: exploiting the cascade carbopalladation reaction between alkynes and gem-dibromoolefins

    Chemical Science · 2013-11-11

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  39. Synthesis, Structure, and Reactivity of Lewis Base Stabilized Plumbacyclopentadienylidenes

    Chemistry - A European Journal · 2013-11-15

    Masaichi Saito, Tomoki Akiba, Misumi Kaneko, Toshiaki Kawamura, Minori Abe, Masahiko Hada, Mao Minoura

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  40. Antiaromaticity in Nonbenzenoid Oligoarenes and Ladder Polymers

    Topics in current chemistry · 2014-01-01

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  41. Functions Incorporating a Halogen and Another Group Other than a Halogen or a Chalcogen

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    B.I. Roman, Thomas S. A. Heugebaert, C.V. Stevens

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  42. Organometallic intermediate-based organic synthesis: organo-di-lithio reagents and beyond

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  43. The B(C6F5)3 Boron Lewis Acid Route to Arene‐Annulated Pentalenes

    Chemistry - An Asian Journal · 2014-03-28

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  44. Facile Synthesis of Dibenzopentalene Dianions and Their Application as New π‐Extended Ligands

    Chemistry - A European Journal · 2014-05-07

    Takuya Kuwabara, Kazuya Ishimura, Takahiro Sasamori, Norihiro Tokitoh, Masaichi Saito

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  45. Enhancement of Stannylene Character in Stannole Dianion Equivalents Evidenced by NMR and Mössbauer Spectroscopy and Theoretical Studies of Newly Synthesized Silyl-Substituted Dilithiostannoles

    Organometallics · 2014-05-23

    Takuya Kuwabara, Jing‐Dong Guo, Shigeru Nagase, Mao Minoura, Rolfe H. Herber, Masaichi Saito

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  46. Intramolecular C–F and C–H bond cleavage promoted by butadienyl heavy Grignard reagents

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    Heng Li, Xiaoye Wang, Baosheng Wei, Ling Xu, Wen‐Xiong Zhang, Jian Pei, Zhenfeng Xi

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  47. A reversible two-electron redox system involving a divalent lead species

    Chemical Communications · 2015-01-01

    Masaichi Saito, M. Nakada, Takuya Kuwabara, Mao Minoura

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  48. Conversion of Zirconacyclopentadienes into Metalloles: Fagan–Nugent Reaction and Beyond

    Accounts of Chemical Research · 2015-04-01

    Xiaoyu Yan, Chanjuan Xi

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  49. π‐Extended Pentalenes: The Revival of the Old Compound from New Standpoints

    The Chemical Record · 2015-04-20

    Takeshi Kawase, Jun‐ichi Nishida

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  50. One-Shot Double Amination of Sondheimer–Wong Diynes: Synthesis of Photoluminescent Dinaphthopentalenes

    Organic Letters · 2015-06-08

    Feng Xu, Lifen Peng, Kenta Shinohara, Takanori Nishida, Kan Wakamatsu, Motoyuki Uejima, Tohru Sato, Kazuyoshi Tanaka, Norihiko Machida, Haruo Akashi, Akihiro Orita, Junzo Otera

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