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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 7
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Original Articles

The Conversion of Carboxylic Acids into Amides via NCS/Triphenylphosphine

Pages 959-968 | Received 31 Aug 1994, Published online: 23 Sep 2006

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Read on this site (10)

Alajos Grün, Mátyás Milen, Tamás Földesi, Péter Ábrányi-Balogh, László Drahos & György Keglevich. (2013) Microwave-Assisted Amidation of Arylacetic Acids by Reaction with 2-Aryl-ethylamines. Synthetic Communications 43:11, pages 1491-1498.
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Hojat Veisi, Ramin Ghorbani-Vaghei & Mohamad Ali Zolfigol. (2011) Recent Progress in the Use of N-Halo Compounds in Organic Synthesis. Organic Preparations and Procedures International 43:6, pages 489-540.
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Ali Khalafi-Nezhad, Abdolkarim Zare, Abolfath Parhami, Mohammad Navid Soltani Rad & Gholam Reza Nejabat. (2007) Silica-Supported 2,4,6-Trichloro-1,3,5-triazine as an Efficient Reagent for Direct Conversion of Carboxylic Acids to Amides Under Solvent-Free Conditions. Phosphorus, Sulfur, and Silicon and the Related Elements 182:3, pages 657-666.
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Min Shi & Shi‐Cong Cui. (2005) Transamidation Catalyzed by a Recoverable and Reusable PolyDMAP‐Based Hafnium Chloride and Montmorillonite KSF. Synthetic Communications 35:22, pages 2847-2858.
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Yunkui Liu & Yongmin Zhang. (2002) TETRAHYDROFURAN RING-OPENING WITH ACYLOXYPHOSPHONIUM IODIDE CATALYZED BY SAMARIUM TRIIODIDE. Organic Preparations and Procedures International 34:2, pages 213-217.
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Sameer P. Dhuru, Nikhil U. Mohe & Manikrao M. Salunkhe. (2001) C-ALKYLATION OF MELDRUM'S ACID USING TRIPHENYL PHOSPHINE AND N-BROMOSUCCINIMIDE. Synthetic Communications 31:23, pages 3653-3657.
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Paul Fr⊘syen. (1997) A NEW METHOD FOR SELECTIVE CONVERSION OF ALCOHOLS TO NITRATES UNDER MILD AND NEUTRAL CONDITIONS. Phosphorus, Sulfur, and Silicon and the Related Elements 129:1, pages 89-97.
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Paul Fr⊘Syen. (1996) One-Flask Conversion of Carboxylic Acids into Carbamoyl Azides. Synthetic Communications 26:24, pages 4549-4561.
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Paul Frøyen & Paul Juvvik. (1996) A NEW METHOD FOR THE CONVERSION OF ALCOHOLS INTO ALKYL IODIDES. Phosphorus, Sulfur, and Silicon and the Related Elements 116:1, pages 217-223.
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P. Veeraraghavan Ramachandran, Henry J. Hamann & Shivani Choudhary. (2020) Amine-boranes as Dual-Purpose Reagents for Direct Amidation of Carboxylic Acids. Organic Letters 22:21, pages 8593-8597.
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Charles D. Irving, Jack T. Floreancig & Sébastien Laulhé. (2020) Amide Synthesis through the In Situ Generation of Chloro- and Imido-Phosphonium Salts. ACS Omega 5:25, pages 15734-15745.
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Kantharaju Kamanna, S.Y. Khatavi & P.B. Hiremath. (2020) Microwave-assisted One-pot Synthesis of Amide Bond using WEB. Current Microwave Chemistry 7:1, pages 50-59.
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Serhat Sezai Çiçek, Arlette Wenzel-Storjohann, Ulrich Girreser & Deniz Tasdemir. (2020) Biological Activities of Two Major Copaiba Diterpenoids and Their Semi-synthetic Derivatives. Revista Brasileira de Farmacognosia 30:1, pages 18-27.
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Socrates B. Munoz, Huong Dang, Xanath Ispizua-Rodriguez, Thomas Mathew & G. K. Surya Prakash. (2019) Direct Access to Acyl Fluorides from Carboxylic Acids Using a Phosphine/Fluoride Deoxyfluorination Reagent System. Organic Letters 21:6, pages 1659-1663.
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Pei-Jiang Chen, Hai-Yang Wang & Ai-Yun Peng. (2015) A mild and efficient amide formation reaction mediated by P(OEt) 3 and iodine . RSC Advances 5:114, pages 94328-94331.
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Sirilak Wangngae, Chuthamat Duangkamol, Mookda Pattarawarapan & Wong Phakhodee. (2015) Significance of reagent addition sequence in the amidation of carboxylic acids mediated by PPh 3 and I 2 . RSC Advances 5:33, pages 25789-25793.
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A. El Kadib, N. Katir, A. Castel, F. Delpech & P. Rivière. (2007) Hydrosilylation of unsaturated fatty acid N ‐phenyl amides . Applied Organometallic Chemistry 21:7, pages 590-594.
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Audrey Farèse, Nadia Patino, Roger Condom, Sandrine Dalleu & Roger Guedj. (1996) Liquid phase synthesis of a peptidic nucleic acid dimer. Tetrahedron Letters 37:9, pages 1413-1416.
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Paul Frøyen & Paul Juvvik. (1995) One-pot synthesis of secondary or tertiary amines from alcohols and amines via alkoxyphosphonium salts. Tetrahedron Letters 36:52, pages 9555-9558.
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P. FROEYEN. (2010) ChemInform Abstract: Conversion of Carboxylic Acids into Amides via NCS/Triphenylphosphine.. ChemInform 26:30.
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