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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 9
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Original Articles

Temperature and Ultrasound Rate Enhancement in the Baylis-Hillman Reaction

Gregory H. P. Roos Department of Chemistry, University of Natal, P. O. Box 375, Pietermaritzburg, 3200, South Africa
&
Pradish Rampersadh Department of Chemistry, University of Natal, P. O. Box 375, Pietermaritzburg, 3200, South Africa
Pages 1261-1266 | Received 24 Nov 1992, Published online: 24 Sep 2006

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Rodrigo Octavio, M. A. de Souza & Mário Luiz A. A. Vasconcellos. (2003) The Use of DMAP as Catalyst in the Baylis-Hillman Reaction Between Methyl Acrylate and Aromatic Aldehydes. Synthetic Communications 33:8, pages 1383-1389.
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Articles from other publishers (37)

Nilton S. Camilo, Hugo Santos, Lucas A. Zeoly, Fábio S. Fernandes, Manoel T. RodriguesJr.Jr., Thiago S. Silva, Samia R. Lima, José Cláudio Serafim, Aline S. B. de Oliveira, Arthur G. Carpanez, Giovanni W. Amarante & Fernando Coelho. (2022) An Improved Protocol for the Morita‐Baylis‐Hillman Reaction Allows Unprecedented Broad Synthetic Scope. European Journal of Organic Chemistry 2022:9.
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Yiheyis Bogale & G. Neelaiah Babu. (2021) Amberlyst A21 catalyzed Morita-Baylis-Hillman reaction. Current Research in Green and Sustainable Chemistry 4, pages 100069.
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Alioune Fall, Insa Seck, Ousmane Diouf, Mohamed Gaye, Matar Seck, Generosa Gómez & Yagamare Fall. (2015) Synthesis of new triazolium-based ionic liquids and their use in the Morita–Baylis–Hillman reaction. Tetrahedron Letters 56:36, pages 5128-5131.
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KODIRAJAN SELVAKUMAR, KANDAPALAM ARUN PRASATH LINGAM, RAMA VARMA LUXMI VARMA & POOVAN SHANMUGAVELAN. (2015) An efficient and facile synthesis of divergent C-3/C-5 bis-functionalized 2-oxindoles from 5-formyl-Morita-Baylis-Hillman adducts of oxindole. Journal of Chemical Sciences 127:8, pages 1417-1426.
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Prashant B. Thorat, Santosh V. Goswami, Bhimrao C. Khade & Sudhakar R. Bhusare. (2012) Organocatalyzed Baylis–Hillman reaction: an enantioselective approach. Tetrahedron: Asymmetry 23:17, pages 1320-1325.
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Min Shi, Feijun Wang, Mei-Xin Zhao & Yin WeiMei-Xin Zhao, Yin Wei & Min Shi. 2011. The Chemistry of the Morita-Baylis-Hillman Reaction. The Chemistry of the Morita-Baylis-Hillman Reaction 1 78 .
Giovanni W. Amarante, Mario Benassi, Humberto M. S. Milagre, Ataualpa A. C. Braga, Feliu Maseras, Marcos N. Eberlin & Fernando Coelho. (2009) Brønsted Acid Catalyzed Morita–Baylis–Hillman Reaction: A New Mechanistic View for Thioureas Revealed by ESI‐MS(/MS) Monitoring and DFT Calculations. Chemistry – A European Journal 15:45, pages 12460-12469.
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Ying Song, Haihua Ke, Nan Wang, Limin Wang & Gang Zou. (2009) Baylis–Hillman reaction promoted by a recyclable protic-ionic-liquid solvent–catalyst system: DABCO–AcOH–H2O. Tetrahedron 65:45, pages 9086-9090.
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Emily Tarsis, Anna Gromova, Daniel Lim, Guoqiang Zhou & Don M. Coltart. (2008) Overcoming the Limitations of the Morita−Baylis−Hillman Reaction: A Rapid and General Synthesis of α-Alkenyl-β′-hydroxy Thioesters. Organic Letters 10:21, pages 4819-4822.
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Shahana Chowdhury, Ram S. Mohan & Janet L. Scott. (2007) Reactivity of ionic liquids. Tetrahedron 63:11, pages 2363-2389.
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Hang Gong, Chang-qun Cai, Nian-fa Yang, Li-wen Yang, Jin Zhang & Qing-hua fan. (2006) Application of non-imidazolium-based ionic liquid in the Baylis–Hillman reactions: Rate and yield promoted. Journal of Molecular Catalysis A: Chemical 249:1-2, pages 236-239.
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Xinyuan Liu, Zhuo Chai, Gang Zhao & Shizheng Zhu. (2005) Aza-Morita-Baylis-Hillman reactions of N-(benzylidene)polyfluoroanilines with methyl acrylate and acrylonitrile. Journal of Fluorine Chemistry 126:8, pages 1215-1221.
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Sanzhong Luo, Peng George Wang & Jin-Pei Cheng. (2003) Remarkable Rate Acceleration of Imidazole-Promoted Baylis−Hillman Reaction Involving Cyclic Enones in Basic Water Solution. The Journal of Organic Chemistry 69:2, pages 555-558.
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R.O.M.A. de Souza & M.L.A.A. Vasconcellos. (2004) Intrinsic catalytic activity of tertiary amines: a mechanistic proposal to the unexpected temperature effect in Baylis–Hillman reaction. Catalysis Communications 5:1, pages 21-24.
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Kiyoshi Ikeda, Yasuhiro Torisawa, Takao Nishi, Junichi Minamikawa, Kiyoshi Tanaka & Masayuki Sato. (2003) Glycosylation of sialyl acetates with a novel catalyst combination: Bismuth triflate and BF3·OEt2 system. Bioorganic & Medicinal Chemistry 11:14, pages 3073-3076.
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A Patra, S Batra, A.P Bhaduri, A Khanna, R Chander & M Dikshit. (2003) Isoxazole-based derivatives from Baylis–Hillman chemistry: assessment of preliminary hypolipidemic activity. Bioorganic & Medicinal Chemistry 11:10, pages 2269-2276.
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Eun Jin Kim, Soo Y. Ko & Choong Eui Song. (2003) Acceleration of the Baylis–Hillman Reaction in the Presence of Ionic Liquids . Helvetica Chimica Acta 86:3, pages 894-899.
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Juexiao Cai, Zhenghong Zhou, Guofeng Zhao & Chuchi Tang. (2002) Dramatic Rate Acceleration of the Baylis−Hillman Reaction in Homogeneous Medium in the Presence of Water. Organic Letters 4:26, pages 4723-4725.
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Yujiro Hayashi, Kotaro Okado, Itaru Ashimine & Mitsuru Shoji. (2002) The Baylis–Hillman reaction under high pressure induced by water-freezing. Tetrahedron Letters 43:48, pages 8683-8686.
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Fernando Coelho, Wanda P. Almeida, Demetrius Veronese, Cristiano R. Mateus, Elizandra C. Silva Lopes, Rodrigo C. Rossi, Gabriel P.C. Silveira & César H. Pavam. (2002) Ultrasound in Baylis–Hillman reactions with aliphatic and aromatic aldehydes: scope and limitations. Tetrahedron 58:37, pages 7437-7447.
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Shū Kobayashi, Masaharu Sugiura, Hidetoshi Kitagawa & William W.-L. Lam. (2002) Rare-Earth Metal Triflates in Organic Synthesis. Chemical Reviews 102:6, pages 2227-2302.
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Tomoya Kitazume, Kenji Tamura, Zaiju Jiang, Noriak Miyake & Isamu Kawasaki. (2002) Synthesis of fluoromethylated materials in ionic liquids. Journal of Fluorine Chemistry 115:1, pages 49-53.
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João N Rosa, Carlos A.M Afonso & António G Santos. (2001) Ionic liquids as a recyclable reaction medium for the Baylis–Hillman reaction. Tetrahedron 57:19, pages 4189-4193.
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Olivier Roy, Abdelkhalek Riahi, Françoise Hénin & Jacques Muzart. (2000) Synergy or Competition between Palladium-Catalysis and KF/Alumina-Mediation for the Allylic Substitution of the Acetates of Baylis–Hillman Adducts by Phenols. Tetrahedron 56:41, pages 8133-8140.
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Mikhail G Sulman. (2000) Effects of ultrasound on catalytic processes. Russian Chemical Reviews 69:2, pages 165-177.
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Tetsuo Iwama, Hironori Kinoshita & Tadashi Kataoka. (1999) 2,6-Diphenyl-4H-chalcogenopyran-4-ones and 2,6-diphenyl-4H-chalcogenopyran-4-thiones: a new catalyst for the Baylis-Hillman reaction. Tetrahedron Letters 40:19, pages 3741-3744.
Crossref
Tadashi Kataoka, Tetsuo Iwama, Shin-ichiro Tsujiyama, Tatsunori Iwamura & Shin-ichi Watanabe. (1998) The chalcogeno-Baylis-Hillman reaction: a new preparation of allylic alcohols from aldehydes and electron-deficient alkenes. Tetrahedron 54:39, pages 11813-11824.
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Jean-Louis LucheChristian Pétrier & Jean-Louis Luche. 1998. Synthetic Organic Sonochemistry. Synthetic Organic Sonochemistry 51 90 .
Linda Joy Brzezinski, Sara Rafel & James W. Leahy. (1997) The asymmetric Baylis-Hillman reaction as a template in organic synthesis. Tetrahedron 53:48, pages 16423-16434.
Crossref
Engelbert Ciganek. 2004. Organic Reactions. Organic Reactions 201 350 .
Deevi Basavaiah, Polisetti Dharma Rao & Rachakonda Suguna Hyma. (1996) The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction. Tetrahedron 52:24, pages 8001-8062.
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Varinder K. Aggarwal, Gary J. Tarver & Ray McCague. (1996) First examples of metal and ligand accelerated catalysis of the Baylis–Hillman reaction. Chem. Commun.:24, pages 2713-2714.
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George M. Strunz, Richard Bethell, Glen Sampson & Peter White. (1995) On the Baylis–Hillman reaction of acrylate, acrylonitrile, and acrolein with some non-enolizable α-dicarbonyl compounds: synthesis of phytotoxic bipolaroxin models. Canadian Journal of Chemistry 73:10, pages 1666-1674.
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Tohru Oishi, Hiroki Oguri & Masahiro Hirama. (1995) Asymmetric Baylis-Hillman reactions using chiral 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes catalysts under high pressure conditions. Tetrahedron: Asymmetry 6:6, pages 1241-1244.
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Jacques Augé, Nadège Lubin & André Lubineau. (1994) Acceleration in water of the Baylis-Hillman reaction. Tetrahedron Letters 35:43, pages 7947-7948.
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G. H. P. ROOS & P. RAMPERSADH. (2010) ChemInform Abstract: Temperature and Ultrasound Rate Enhancement in the Baylis‐Hillman Reaction.. ChemInform 24:47.
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E.Peter Kündig, He Xu Long, Patrick Romanens & Gérald Bernardinelli. (1993) Highly diastereoselective coupling reactions between chiral benzaldehyde tricarbonylchromium complexes and activated double bonds. Tetrahedron Letters 34:44, pages 7049-7052.
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