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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 22
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Original Articles

Iodoform, a New Reagent in the Todd-Atherton Reaction

Grażyna Mielniczak Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Łódź, Poland
&
Dr. Andrzej Bopusiński Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Łódź, PolandCorrespondence[email protected]
Pages 3851-3859 | Received 08 Apr 2003, Published online: 19 Aug 2006

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SK. Nayab Rasool, P. Hari Babu, D. B. Janaki Ramudu, M. V. Jyothi Kumar, Ch. Appa Rao & C. Naga Raju. (2018) Synthesis and bioactivity evaluation of new phenyl N,N′-phenylphosphorodiamidates. Phosphorus, Sulfur, and Silicon and the Related Elements 193:1, pages 10-13.
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Wafaa M. Abdou, Reham F. Barghash & Mohamed S. Bekheit. (2015) Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates. Synthetic Communications 45:17, pages 1929-1963.
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Juan Huang, Wen He & Bin Wang. (2012) Bu4NI-Catalyzed Synthesis of Pyrophosphate Esters from H-Phosphonates. Phosphorus, Sulfur, and Silicon and the Related Elements 187:10, pages 1125-1131.
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Articles from other publishers (31)

Danupat Beukeaw, Napassawan Rattanasupaponsak, Tanakorn Kittikool, Kunita Phakdeeyothin, Khampee PhomphraiSirilata Yotphan. (2022) Metal‐Free Site‐Selective Direct Oxidative Phosphorylation of Pyrazolones. Advanced Synthesis & Catalysis 364:17, pages 3066-3073.
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Axel Sabourin, Jeremy Dufour, Jean‐Pierre Vors, David Bernier & Jean‐Luc Montchamp. (2022) Synthesis of Carbon‐ and Nitrogen‐Substituted 5‐ and 6‐Membered Benzophostams. European Journal of Organic Chemistry 2022:16.
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Yushi Tan, Ya-Ping Han, Yuecheng Zhang, Hong-Yu Zhang, Jiquan Zhao & Shang-Dong Yang. (2022) Primary Amination of Ar 2 P(O)–H with (NH 4 ) 2 CO 3 as an Ammonia Source under Simple and Mild Conditions and Its Extension to the Construction of Various P–N or P–O Bonds . The Journal of Organic Chemistry 87:5, pages 3254-3264.
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Xin‐Hua Peng, Rui Bai, Shanshan Liu, Zhuo Li & Lin‐Yu Jiao. (2021) Substitution of diarylphosphoryl azides with aliphatic amines catalyzed by simple rare‐earth metal salts: Efficient and novel preparation of phosphoryl amides. Applied Organometallic Chemistry 36:2.
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Axel Sabourin, Jeremy Dufour, Jean-Pierre Vors, David Bernier & Jean-Luc Montchamp. (2021) Synthesis of P -Substituted 5- and 6-Membered Benzo-Phostams: 2,3-Dihydro-1 H -1,2-benzazaphosphole 2-Oxides and 2,3-Tetrahydro-1 H -1,2-benzazaphosphinine 2-Oxides . The Journal of Organic Chemistry 86:21, pages 14684-14694.
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Lin-Yu Jiao, Xin-Hua Peng, Ze-Lin Wang, Nan Jia & Zhuo Li. (2021) When phosphoryl azide meets mechanochemistry: clean, rapid, and efficient synthesis of phosphoryl amides under B(C 6 F 5 ) 3 catalysis in a ball mill . Catalysis Science & Technology 11:20, pages 6659-6665.
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Karen R. Winters & Jean-Luc Montchamp. (2020) Evaluation and Development of Methodologies for the Synthesis of Thiophosphinic Acids. The Journal of Organic Chemistry 85:22, pages 14545-14558.
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Yingcong Ou, Yuanting Huang, Zhenlin He, Guodian Yu, Yanping Huo, Xianwei Li, Yang Gao & Qian Chen. (2020) A phosphoryl radical-initiated Atherton–Todd-type reaction under open air. Chemical Communications 56:9, pages 1357-1360.
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Thippani Anitha, Kashamalla Chinna Ashalu, Mummadi Sandeep, Aabid Mohd, Joanna Wencel-Delord, Francoise Colobert & Kallu Rajender Reddy. (2019) LiI/TBHP Mediated Oxidative Cross-Coupling of P(O)-H Compounds with Phenols and Various Nucleophiles: Direct Access to the Synthesis of Organophosphates. European Journal of Organic Chemistry 2019:45, pages 7463-7474.
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Qing Li, Xiaohua Sun, Xiaoqin Yang, Minghu Wu, Shaofa Sun & Xiuling Chen. (2019) Transition-metal-free amination phosphoryl azide for the synthesis of phosphoramidates. RSC Advances 9:28, pages 16040-16043.
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Chi Woo Ahn, Hosung Ki, Joonghan Kim, Jeongho Kim, Sungjun Park, Yunbeom Lee, Kyung Hwan Kim, Qingyu Kong, Jiwon Moon, Martin Nors Pedersen, Michael Wulff & Hyotcherl Ihee. (2018) Direct Observation of a Transiently Formed Isomer During Iodoform Photolysis in Solution by Time-Resolved X-ray Liquidography. The Journal of Physical Chemistry Letters 9:3, pages 647-653.
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Xunwei Chen, Zecai Xiao, Hanyu Chu, Bo Wang & Ai-Yun Peng. (2018) Reinvestigation of the iodine-mediated phosphoramidation reaction of amines and P(OR) 3 and its synthetic applications . Organic & Biomolecular Chemistry 16:36, pages 6783-6790.
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Kolio D. Troev. 2018. Reactivity of P-H Group of Phosphorus Based Compounds. Reactivity of P-H Group of Phosphorus Based Compounds 291 409 .
Yoseph G. Daniel & Bob A. Howell. (2017) Synthesis and characterization of isosorbide bis -phosphorus esters . Heteroatom Chemistry 28:3, pages e21369.
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Leila Bahri, T. Barhoumi-Slimi, R. Mallek, M.A.K. Sanhoury, B. Crousse & M.T. Ben Dhia. (2016) One-pot synthesis of new highly substituted allylic phosphorodiamidates. Journal of Fluorine Chemistry 189, pages 96-101.
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John M. Read, Yu‐Pu Wang & Rick L. Danheiser*. 2003. Organic Syntheses. Organic Syntheses 156 170 .
Babak Kaboudin, Foad Kazemi & Fereshteh Habibi. (2015) Fe3O4@MgO nanoparticles as an efficient recyclable catalyst for the synthesis of phosphoroamidates via the Atherton–Todd reaction. Tetrahedron Letters 56:46, pages 6364-6367.
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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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Shan Li, Tieqiao Chen, Yuta Saga & Li-Biao Han. (2015) Chloroform-based Atherton–Todd-type reactions of alcohols and thiols with secondary phosphine oxides generating phosphinothioates and phosphinates. RSC Advances 5:88, pages 71544-71546.
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Christopher M. Timperley, Pierre-Yves Renard & Catherine Gomez. 2015. Best Synthetic Methods. Best Synthetic Methods 365 562 .
Hyunwoo Kim, Juhyeon Park, Jeung Gon Kim & Sukbok Chang. (2014) Synthesis of Phosphoramidates: A Facile Approach Based on the C–N Bond Formation via Ir-Catalyzed Direct C–H Amidation. Organic Letters 16:20, pages 5466-5469.
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Stéphanie S Le Corre, Mathieu Berchel, Hélène Couthon-Gourvès, Jean-Pierre Haelters & Paul-Alain Jaffrès. (2014) Atherton–Todd reaction: mechanism, scope and applications. Beilstein Journal of Organic Chemistry 10, pages 1166-1196.
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P.R. Hanson, N. Asad, Q. Zang, S. Jayashinghe & J. Markley. 2014. Comprehensive Organic Synthesis II. Comprehensive Organic Synthesis II 479 554 .
Reda A. Haggam & Uwe Beifuss. (2012) WITHDRAWN: Efficient transformation of nitroarenes into dialkyl N-arylphosphoramidates in one step under microwave conditions. Tetrahedron.
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Sebastian Wagner, Muriel Rakotomalala, Yana Bykov, Olaf Walter & Manfred Döring. (2012) Synthesis of new organophosphorus compounds using the atherton–todd reaction as a versatile tool. Heteroatom Chemistry 23:2, pages 216-222.
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Reda Haggam, Jürgen Conrad & Uwe Beifuss. (2009) Practical and reliable synthesis of dialkyl N-arylphosphoramidates with nitroarenes as substrates. Tetrahedron Letters 50:48, pages 6627-6630.
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Atsushi Goto, Norihiro Hirai, Yoshinobu Tsujii & Takeshi Fukuda. (2008) Reversible Chain Transfer Catalyzed Polymerizations (RTCPs) of Styrene and Methyl Methacrylate with Phosphorus Catalysts. Macromolecular Symposia 261:1, pages 18-22.
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Atsushi Goto, Hirokazu Zushi, Norihiro Hirai, Tsutomu Wakada, Yoshinobu Tsujii & Takeshi Fukuda. (2007) Living Radical Polymerizations with Germanium, Tin, and Phosphorus Catalysts − Reversible Chain Transfer Catalyzed Polymerizations (RTCPs). Journal of the American Chemical Society 129:43, pages 13347-13354.
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David Crich, Milan Bruncko, Jarmila Brunckova, Xiaoling Lu & Robert S. Coleman. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Peter R. Schreiner & Andrey A. Fokin. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Grazyna Mielniczak & Andrzej Lopusinski. (2004) Iodoform, a New Reagent in the Todd—Atherton Reaction.. ChemInform 35:11.
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