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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 11
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Original Articles

New Preparation of Bromoallenes

Michel Montury Laboratoire de Chimie Organique I, Université Claude Bernard Lyon I, 43 Boulevard du 11 Novembre 1918, 69622, Villeurbanne, France
&
Jacques Goré Laboratoire de Chimie Organique I, Université Claude Bernard Lyon I, 43 Boulevard du 11 Novembre 1918, 69622, Villeurbanne, France
Pages 873-879 | Published online: 06 Dec 2006

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Jiong Chun, Jingyu Sun & Weihui Deng. (2020) Synthesis of new ceramide analogues with allene in the sphingoid backbone. Synthetic Communications 50:20, pages 3149-3157.
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Articles from other publishers (51)

Rongyu Sun, Emilie Viaud, Rajesh Nomula, Jean‐Valère Naubron, Nicolas Daugey, Thierry Buffeteau, Frédéric Castet, Patrick Y. Toullec, Stéphane Quideau & Philippe A. Peixoto. (2023) Asymmetric Allenylation of Alkynes mediated by Chiral Organoselenated Reagents under Oxidative Conditions. Angewandte Chemie International Edition 62:42.
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Rongyu Sun, Emilie Viaud, Rajesh Nomula, Jean‐Valère Naubron, Nicolas Daugey, Thierry Buffeteau, Frédéric Castet, Patrick Y. Toullec, Stéphane Quideau & Philippe A. Peixoto. (2023) Asymmetric Allenylation of Alkynes mediated by Chiral Organoselenated Reagents under Oxidative Conditions. Angewandte Chemie 135:42.
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Yunhe Lv, Junrong Lai, Weiya Pu, Jin Wang, Wanru Han, Axue Wang, Mengyue Zhang & Xue Wang. (2023) Metal-Free Highly Regioselective 1,4-Sulfonyliodination of 1,3-Enynes. The Journal of Organic Chemistry 88:4, pages 2034-2045.
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Uma Maheshwar Gonela & Jhillu S. Yadav. (2020) Synthesis of chiral propargyl alcohols following the base-induced elimination protocol: application in the total synthesis of natural products. New Journal of Chemistry 44:13, pages 4972-4986.
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Marie Vayer, Régis Guillot, Christophe Bour & Vincent Gandon. (2018) Synthesis of 3-Substituted 3-Bromo-1-phenylallenes from Alkynylcycloheptatrienes. The Journal of Organic Chemistry 83:18, pages 11309-11317.
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Te‐ik Sohn, Deukjoon Kim & Robert S. Paton. (2015) Substrate‐Controlled Asymmetric Total Syntheses of Microcladallenes A, B, and C Based on the Proposed Structures. Chemistry – A European Journal 21:45, pages 15988-15997.
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Akira Iwata, Shinsuke Inuki, Shinya Oishi, Nobutaka Fujii & Hiroaki Ohno. (2015) Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides. Tetrahedron 71:37, pages 6580-6585.
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Jörg Erdsack & Norbert Krause. (2013) An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (α S ,2 R )-(2,5-dihydro-1 H -pyrrol-2-yl)glycine . Beilstein Journal of Organic Chemistry 9, pages 1936-1942.
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Hiroaki Chiba, Yuki Sakai, Ayako Ohara, Shinya Oishi, Nobutaka Fujii & Hiroaki Ohno. (2013) Convergent Synthesis of (−)‐Quinocarcin Based on the Combination of Sonogashira Coupling and Gold(I)‐Catalyzed 6‐ endo ‐ dig Hydroamination . Chemistry – A European Journal 19:27, pages 8875-8883.
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Yuji Yoshimitsu, Shinsuke Inuki, Shinya Oishi, Nobutaka Fujii & Hiroaki Ohno. (2013) Palladium-Catalyzed Medium-Ring Formation for Construction of the Core Structure of Laurencia Oxacycles: Synthetic Study of Laurendecumallene B . Organic Letters 15:12, pages 3046-3049.
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Mi Jung Kim, Te-ik Sohn, Deukjoon Kim & Robert S. Paton. (2012) Concise Substrate-Controlled Asymmetric Total Syntheses of Dioxabicyclic Marine Natural Products with 2,10-Dioxabicyclo-[7.3.0]dodecene and 2,9-Dioxabicyclo[6.3.0]undecene Skeletons. Journal of the American Chemical Society 134:49, pages 20178-20188.
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Hiroaki Chiba, Shinya Oishi, Nobutaka Fujii & Hiroaki Ohno. (2012) Total Synthesis of (−)‐Quinocarcin by Gold(I)‐Catalyzed Regioselective Hydroamination. Angewandte Chemie International Edition 51:36, pages 9169-9172.
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Hiroaki Chiba, Shinya Oishi, Nobutaka Fujii & Hiroaki Ohno. (2012) Total Synthesis of (−)‐Quinocarcin by Gold(I)‐Catalyzed Regioselective Hydroamination. Angewandte Chemie 124:36, pages 9303-9306.
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Wen Feng Jiang, Xue Song Liu, Xin Du, Jian Wei Wei & Chun Yu Bao. (2012) Facile synthesis of bromoallenes via N-bromosuccinimide/CH3SCH3 for the bromination of propargyl alcohols. Chinese Chemical Letters 23:9, pages 999-1002.
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Shinsuke InukiShinsuke Inuki. 2012. Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds. Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds 11 27 .
Shichao Yu & Shengming Ma. (2011) How easy are the syntheses of allenes?. Chemical Communications 47:19, pages 5384-5418.
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Matthias A. Schade, Shigeyuki Yamada & Paul Knochel. (2011) Synthesis of Polyfunctional Allenes by Successive Copper‐Mediated Substitutions. Chemistry – A European Journal 17:15, pages 4232-4237.
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Deepak V. Dekhane, Shivaji S. Pawar, Sunil V. Gupta, Murlidhar S. Shingare & Shivaji N. Thore. (2010) Lithium bromide catalyzed solvent free method for synthesis of 2-substituted benzimidazoles and imidazopyridines. Chinese Chemical Letters 21:5, pages 519-523.
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Yan Zhang & Yikang Wu. (2010) An enantioselective total synthesis of natural antibiotic marasin. Organic & Biomolecular Chemistry 8:20, pages 4744.
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Shinsuke Inuki, Yuji Yoshimitsu, Shinya Oishi, Nobutaka Fujii & Hiroaki Ohno. (2009) Ring-Construction/Stereoselective Functionalization Cascade: Total Synthesis of Pachastrissamine (Jaspine B) through Palladium-Catalyzed Bis-cyclization of Bromoallenes. Organic Letters 11:19, pages 4478-4481.
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Wen Zhang, Huadong Xu, Hui Xu & Weiping Tang. (2009) DABCO-Catalyzed 1,4-Bromolactonization of Conjugated Enynes: Highly Stereoselective Formation of a Stereogenic Center and an Axially Chiral Allene. Journal of the American Chemical Society 131:11, pages 3832-3833.
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K. C. Nicolaou, Jason S. Chen, David J. Edmonds & Anthony A. Estrada. (2009) Recent Advances in the Chemistry and Biology of Naturally Occurring Antibiotics. Angewandte Chemie International Edition 48:4, pages 660-719.
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K. C. Nicolaou, Jason S. Chen, David J. Edmonds & Anthony A. Estrada. (2009) Fortschritte in der Chemie und Biologie natürlicher Antibiotika. Angewandte Chemie 121:4, pages 670-732.
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Yu Tang, Lichun Shen, Becky J. Dellaria & Richard P. Hsung. (2008) Saucy–Marbet rearrangements of alkynyl halides in the synthesis of highly enantiomerically enriched allenyl halides. Tetrahedron Letters 49:45, pages 6404-6409.
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Ya-Jun Jian, Chao-Jun Tang & Yikang Wu. (2007) Enantioselective Total Synthesis of Phomallenic Acid C. The Journal of Organic Chemistry 72:13, pages 4851-4855.
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Hisao Hamaguchi, Shohei Kosaka, Hiroaki Ohno, Nobutaka Fujii & Tetsuaki Tanaka. (2007) Bromoallenes as Allyl Dication Equivalents in the Presence or Absence of Palladium(0): Direct Construction of Bicyclic Sulfamides Containing Five‐ to Eight‐membered Rings by Tandem Cyclization of Bromoallenes. Chemistry – A European Journal 13:6, pages 1692-1708.
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Anna Maria Caporusso, Alessia Zampieri, Laura Antonella Aronica & Donatella Banti. (2006) Stereoselective Synthesis of Chiral 3-Aryl-1-alkynes from Bromoallenes and Heterocuprates. The Journal of Organic Chemistry 71:5, pages 1902-1910.
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Hiroaki OHNO. (2005) Development of Useful Reactions Based on the Novel Reactivities of Allenic Compounds and Their Application to Tandem Cyclizationsアレン系化合物の新しい反応性に基づく有用反応の開発と連続環化反応への展開. YAKUGAKU ZASSHI 125:12, pages 899-925.
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Barry M. Trost & Dylan T. Stiles. (2005) Synthesis of Allenamides by Copper-Catalyzed Coupling of Allenyl Halides with Amides, Carbamates, and Ureas. Organic Letters 7:11, pages 2117-2120.
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Hisao Hamaguchi, Shohei Kosaka, Hiroaki Ohno & Tetsuaki Tanaka. (2005) Bromoallenes as Allyl Dication Equivalents in the Absence of Palladium( 0 ): Synthesis of Bicyclic Sulfamides by Tandem Cyclization of Bromoallenes . Angewandte Chemie International Edition 44:10, pages 1513-1517.
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Hisao Hamaguchi, Shohei Kosaka, Hiroaki Ohno & Tetsuaki Tanaka. (2005) Bromoallenes as Allyl Dication Equivalents in the Absence of Palladium( 0 ): Synthesis of Bicyclic Sulfamides by Tandem Cyclization of Bromoallenes . Angewandte Chemie 117:10, pages 1537-1541.
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Hiroaki Ohno. (2005) Development of Useful Reactions Involving Tandem Cyclizations Based on the Novel Reactivities of Allenic Compounds. CHEMICAL & PHARMACEUTICAL BULLETIN Chemical and Pharmaceutical Bulletin 53:10, pages 1211-1226.
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Hiroaki Ohno, Yasuo Nagaoka & Kiyoshi Tomioka. 2004. Modern Allene Chemistry. Modern Allene Chemistry 141 181 .
Hiroaki Ohno, Hisao Hamaguchi, Miyo Ohata, Shohei Kosaka & Tetsuaki Tanaka. (2004) Palladium(0)-Catalyzed Synthesis of Medium-Sized Heterocycles by Using Bromoallenes as an Allyl Dication Equivalent. Journal of the American Chemical Society 126:28, pages 8744-8754.
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Tetsuaki Tanaka, Hiroaki Ohno, Hisao Hamaguchi, Miyo Ohata & Shohei Kosaka. (2003) Novel Synthesis of Azocine, Azepine, Oxocine, and Oxepine Derivatives by Palladium-catalyzed Medium-Ring Formation from Bromoallenes. HETEROCYCLES 61:1, pages 65.
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Hiroaki Ohno, Kaori Ando, Hisao Hamaguchi, Yusuke Takeoka & Tetsuaki Tanaka. (2002) A Highly cis -Selective Synthesis of 2-Ethynylaziridines by Intramolecular Amination of Chiral Bromoallenes:  Improvement of Stereoselectivity Based on the Computational Investigation . Journal of the American Chemical Society 124:51, pages 15255-15266.
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Michael T Crimmins, Kyle A Emmitte & Allison L Choy. (2002) Ring closing metathesis for the formation of medium ring ethers: the total synthesis of (−)-isolaurallene. Tetrahedron 58:10, pages 1817-1834.
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An-Hsuan Feng, Jyh-Yang Chen, Lian-Ming Yang, Gene-Hsiang Lee, Yu Wang & Tien-Yau Luh. (2001) Unexpected Lewis Acid-Mediated Dimerization of 1,3-Diarylpropargylic Alcohols. The Journal of Organic Chemistry 66:23, pages 7922-7924.
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Hiroaki Ohno, Hisao Hamaguchi & Tetsuaki Tanaka. (2001) Stereoselective Synthesis of Chiral 2,3- cis -2-Ethynylaziridines by Base-Mediated Intramolecular Amination of Bromoallenes . Organic Letters 3:15, pages 2269-2271.
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James A. Marshall & Charsetta M. Grant. (1999) Preparation of Chiral Allenylmetal Reagents from Enantioenriched Allenyl Iodides and Propargylic Mesylates. A Comparison of Indium, Bismuth, and Tin Derivatives. The Journal of Organic Chemistry 64:22, pages 8214-8219.
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Fabrice Chemla, Nicolas Bernard & Jean Normant. (1999) A New Diastereodivergent Synthesis of 1,2-Disubstituted Homopropargylic Alcohols. European Journal of Organic Chemistry 1999:9, pages 2067-2078.
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Arno G. Steinig & Armin de Meijere. (1999) Palladium-Catalyzed Bicyclization of 2-Bromo-1,6-dienes and -1,6-enynes to 5-Membered-Ring-Annelated Vinylcyclopropane Derivatives. European Journal of Organic Chemistry 1999:6, pages 1333-1344.
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Fabiana D'Aniello, Andr? Mann, Ang?le Schoenfelder & Maurizio Taddei. (1997) Stereoconvergent synthesis of (2S,3S,8S,9S,4E,6E)-N-Boc-ADDA starting from (S)-serine and (S)-phenyllactic acid. Tetrahedron 53:4, pages 1447-1456.
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F. D'Aniell, A. Mann & M. Taddei. (1996) 1,3-Stereocontrol with Bromoallenes. Synthesis of N -Boc-ADDA, the Unique Amino Acid Present in Several Inhibitors of Serine/Threonine Phosphatases . The Journal of Organic Chemistry 61:15, pages 4870-4871.
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Carmela Polizzi, Carla Consoloni, Luciano Lardicci & Anna Maria Caporusso. (1991) Reaction of 1-bromo-1,2-dienes with alkylcuprates as a regio- and stereo-selective route to acetylenic or allenic compounds. Journal of Organometallic Chemistry 417:1-2, pages 289-304.
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Björn M. Nilsson & Uli Hacksell. (2009) Base‐Catalyzed cyclization of N ‐propargylamides to oxazoles . Journal of Heterocyclic Chemistry 26:2, pages 269-275.
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Gerrit L'abbé. (2010) Are Azidocumulenes Accessible?. Bulletin des Sociétés Chimiques Belges 93:7, pages 579-592.
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Gerrit L'abbé, Michel Mahy, Marcus Bollyn, Gabriel Germain & Guy Scheefer. (2010) Approaches Towards the Synthesis of Allenyl Azides. Bulletin des Sociétés Chimiques Belges 92:10, pages 881-891.
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Louis S. Hegedus. (1982) Transition metals in organic synthesis annual survey covering the year 1980. Journal of Organometallic Chemistry 237, pages 231-450.
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M. MONTURY & J. GORE. (2016) ChemInform Abstract: NEW PREPARATION OF BROMOALLENES. Chemischer Informationsdienst 12:13.
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