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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 2
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Original Articles

Synthesis of Novel Functionalized N-Tosylaldimines

James H. Wynne Department of Chemistry, George Mason University, Fairfax, Virginia, USA
,
Stacy E. Price Department of Chemistry, George Mason University, Fairfax, Virginia, USA
,
Jeffrey R. Rorer Department of Chemistry, George Mason University, Fairfax, Virginia, USA
&
Wayne M. Stalick Department of Chemistry, George Mason University, Fairfax, Virginia, USA; Department of Chemistry, George Mason University, 4400 University Drive, Fairfax, VA 22030, USACorrespondence[email protected]
Pages 341-352 | Received 22 Feb 2002, Published online: 21 Aug 2006

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Zhenjiang Li, Xinhua Ren, Yuhu Shi & Pingkai Ouyang. (2007) Practical and General Entry to N‐Tosyl Aryl Aldimines Promoted by Sulfamic Acid in Water and Alcohol. Synthetic Communications 37:5, pages 713-724.
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Articles from other publishers (34)

Marine Pinaud, Emilie Plantiveau, Eric Huet, Erwan Le Gall & Marc Presset. (2023) Mannich‐Type Reactions of Alkylzinc Reagents. European Journal of Organic Chemistry.
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Souvik Guha, Ritwik Bhattacharya, Jesni Jacob, Mahesh Ravva & Subhabrata Sen. (2023) Metal-free synthesis of N -sulfonyl imines from benzyl alcohol derivatives and iminoiodinanes via mechanochemistry . Organic & Biomolecular Chemistry.
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Megan D. Hopkins, Felagot A. Abebe, Kristina A. Scott, Garett L. Ozmer, Alec A. Sheir, Lucas J. Schroeder, Robert J. Sheaff & Angus A. Lamar. (2019) Synthesis and identification of heteroaromatic N -benzyl sulfonamides as potential anticancer agents . Organic & Biomolecular Chemistry 17:36, pages 8391-8402.
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Akram Ashouri, Saadi Samadi, Behzad Nasiri & Zohre Bahrami. (2019) Iron-based nanomaterials used as magnetic mesoporous nanocomposites to catalyze the preparation of N-sulfonylimines. Comptes Rendus Chimie 22:8, pages 549-556.
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Megan Hopkins, Zachary Brandeburg, Andrew Hanson & Angus Lamar. (2018) Visible-Light, Iodine-Promoted Formation of N-Sulfonyl Imines and N-Alkylsulfonamides from Aldehydes and Hypervalent Iodine Reagents. Molecules 23:8, pages 1838.
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V. Prakash Reddy, Meher Perambuduru & Jatin Mehta. (2018) N-Heterocyclic Carbene-Catalyzed Trifluoromethylation of Aromatic N-Tosylaldimines. Topics in Catalysis 61:7-8, pages 699-703.
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Megan D. Hopkins, Kristina A. Scott, Brettany C. DeMier, Heather R. Morgan, Jesse A. Macgruder & Angus A. Lamar. (2017) Formation of N-sulfonyl imines from iminoiodinanes by iodine-promoted, N-centered radical sulfonamidation of aldehydes. Organic & Biomolecular Chemistry 15:43, pages 9209-9216.
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Dayun Huang, Xuesong Wang, Xingyong Wang, Wenwen Chen, Xinyan Wang & Yuefei Hu. (2016) Synthesis of N -Sulfonyl Arylaldimines Developed by Retesting an Old Process . Organic Letters 18:3, pages 604-607.
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Chao Wu, Wangyong Huang, Weimin He & Jiannan Xiang. (2013) One-pot Preparation of Homopropargylic N -Sulfonylamines Catalyzed by Zinc Powder . Chemistry Letters 42:10, pages 1233-1234.
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Tom Boultwood, Dominic P. Affron, Aaron D. Trowbridge & James A. Bull. (2013) Synthesis of cis - C -Iodo -N -Tosyl-Aziridines using Diiodomethyllithium: Reaction Optimization, Product Scope and Stability, and a Protocol for Selection of Stationary Phase for Chromatography . The Journal of Organic Chemistry 78:13, pages 6632-6647.
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Angupillai Satheshkumar & Kuppanagounder P. Elango. (2013) Intermolecular charge transfer facilitated synthesis and spectral characterization of Schiff bases of a weak nucleophile 2,3-diamino-1,4-naphthoquinone. RSC Adv. 3:5, pages 1502-1508.
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Xun Zhu & Yunyang Wei. (2012) Synthesis of N-Sulfonylimines Using CeCl 3 Under Neutral Conditions . Journal of Chemical Research 36:6, pages 363-364.
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María Durán-Galván & Brian T. Connell. (2011) Synthesis of 2-amino-1,3-dienes by chromium-catalyzed addition of silylated propargyl bromides to imines. Tetrahedron 67:41, pages 7901-7908.
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Haibo Mei, Xiaoyun Ji, Jianlin Han & Yi Pan. (2011) Tetrabenzylhafnium as a New Organometallic Reagent for Imine Addition Resulting in α-Branched Amines. European Journal of Organic Chemistry 2011:29, pages 5783-5786.
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Yizhe Yan, Kun Xu, Yang Fang & Zhiyong Wang. (2011) A Catalyst-Free Benzylic C–H Bond Olefination of Azaarenes for Direct Mannich-like Reactions. The Journal of Organic Chemistry 76:16, pages 6849-6855.
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Gui Sheng Deng, Jing Yuan Zou & Teng Fei Sun. (2011) Efficient and convenient preparation of N-tosylimines catalyzed by indium trichloride. Chinese Chemical Letters 22:5, pages 511-514.
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Rajesh Patel, Vishnu P. Srivastava & Lal Dhar S. Yadav. (2010) The First Example of Saccharin‐Lithium Bromide Catalysis: Direct Synthesis of N ‐Tosylimines from Alcohols . Advanced Synthesis & Catalysis 352:10, pages 1610-1614.
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André B. Charette. 2010. Chiral Amine Synthesis. Chiral Amine Synthesis 1 49 .
Paula Sério Branco, Vivek Prabhakar Raje, Jorge Dourado & Joana Gordo. (2010) Catalyst-free aziridination and unexpected homologation of aziridines from imines. Organic & Biomolecular Chemistry 8:13, pages 2968.
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Xiao-Feng Wu, Chloé Vovard-Le Bray, Lazhar Bechki & Christophe Darcel. (2009) Iron-catalyzed sulfonylimine synthesis under neutral conditions. Tetrahedron 65:36, pages 7380-7384.
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Hao Sun, Fang-Zheng Su, Ji Ni, Yong Cao, He-Yong He & Kang-Nian Fan. (2009) Gold Supported on Hydroxyapatite as a Versatile Multifunctional Catalyst for the Direct Tandem Synthesis of Imines and Oximes. Angewandte Chemie International Edition 48:24, pages 4390-4393.
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Hao Sun, Fang-Zheng Su, Ji Ni, Yong Cao, He-Yong He & Kang-Nian Fan. (2009) Gold Supported on Hydroxyapatite as a Versatile Multifunctional Catalyst for the Direct Tandem Synthesis of Imines and Oximes. Angewandte Chemie 121:24, pages 4454-4457.
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Renhua Fan, Dongming Pu, Fengqi Wen, Yang Ye & Xiaoli Wang. (2008) A Facile Synthesis of N -Sulfonyl and N -Sulfinyl Aldimines under Barbier-Type Conditions . The Journal of Organic Chemistry 73:9, pages 3623-3625.
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Ming-Juan Qi & Min Shi. (2007) Aza-Baylis–Hillman reaction of salicyl N-tosylimines with methyl vinyl ketone, ethyl vinyl ketone or phenyl vinyl ketone. Tetrahedron 63:42, pages 10415-10424.
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Yong‐Ling Shi & Min Shi. (2007) Chiral Thiourea‐Phosphine Organocatalysts in the Asymmetric Aza‐Morita–Baylis–Hillman Reaction. Advanced Synthesis & Catalysis 349:13, pages 2129-2135.
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Min Shi, Ying-Wen Guo & Hong-Bin Li. (2007) Baylis-Hillman Reactions of Sulfonyl Aldimines or Aryl Aldehydes with 3-Methylpenta-3,4-dien-2-one or 3-Benzylpenta-3,4-dien-2-one. Chinese Journal of Chemistry 25:6, pages 828-835.
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Ying-Wen Guo, Yong-Ling Shi, Hong-Bin Li & Min Shi. (2006) Reactions of salicyl N-tosylimines or salicylaldehydes with diethyl acetylenedicarboxylate for the synthesis of highly functionalized chromenes. Tetrahedron 62:25, pages 5875-5882.
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Ying-Hao Liu, Lian-Hui Chen & Min Shi. (2006) Asymmetric Aza-Morita–BaylisHillman Reaction ofN-Sulfonated Imines with Activated Olefins Catalyzed by Chiral Phosphine Lewis Bases Bearing Multiple Phenol Groups. Advanced Synthesis & Catalysis 348:7-8, pages 973-979.
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Yong-Ling Shi & Min Shi. (2006) Synthesis of Substituted Chromenes through the DABCO-Catalyzed Reaction of But-3-yn-2-one and Methyl Propiolate with SalicylN-Tosylimines (DABCO=1,4-diazabicyclo[2.2.2]octane). Chemistry - A European Journal 12:12, pages 3374-3378.
Crossref
Zhenjiang Li, Xinghua Ren, Ping Wei, Honggui Wan, Yuhu Shi & Pingkai Ouyang. (2006) A convenient preparation of aliphatic and aromatic N-sulfonylimines mediated by sulfamic acid in aqueous media. Green Chemistry 8:5, pages 433.
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Marc David & Danièle Bonnet-Delpon. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
S. Rossiter & A.P. Dobbs. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 451 467 .
James H. Wynne, Stacy E. Price, Jeffrey R. Rorer & Wayne M. Stalick. (2003) Synthesis of Novel Functionalized N‐Tosylaldimines.. ChemInform 34:21.
Crossref
James H. Wynne, Samuel D. Jensen, Christopher T. Lloyd, Wayne M. Stalick & Arthur W. Snow. 2003. 19th International Congress on Heterocyclic Chemistry. 19th International Congress on Heterocyclic Chemistry 363 .

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