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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 6
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Original Articles

Improved Methods for the Oxidation of Secondary Amines to Nitroxides

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Pages 409-413 | Received 16 May 1975, Published online: 06 Dec 2006

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Douglas VQ. Nunes, Cristiane A. Costa, Graziele F. De Bem, Viviane SC. Cordeiro, Izabelle B. Santos, Lenize CRM. Carvalho, Alessandro K. Jordão, Anna C Cunha, Vitor F Ferreira, Roberto S Moura, Angela C. Resende & Dayane T. Ognibene. (2018) Tempol, a superoxide dismutase-mimetic drug, prevents chronic ischemic renal injury in two-kidney, one-clip hypertensive rats. Clinical and Experimental Hypertension 40:8, pages 721-729.
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Harender Singh Bisht & Alok Kumar Chatterjee. (2001) LIVING FREE-RADICAL POLYMERIZATION—A REVIEW. Journal of Macromolecular Science, Part C 41:3, pages 139-173.
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GregoryP. Hamill, ElizabethA. Yost & DanielJ. Sandman. (1992) 4, 4′-(butadiyne-l, 4-diyl)-bis-(2, 2, 6, 6-tetramethyl-4-hydroxypiperidin-1 -oxyl): A Convenient Synthesis and a Polymorphic Transformation Induced by Ionizing Radiation. Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals 211:1, pages 339-345.
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Articles from other publishers (47)

Dirk Leifert & Armido Studer. (2023) Organic Synthesis Using Nitroxides. Chemical Reviews 123:16, pages 10302-10380.
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Camila S. França, Dayanne L. Porto, Joadir H. S. Junior, Fábio S. Souza, Ticiano G. Nascimento, Fernando H. A. Nogueira, Ana P. B. Gomes, Alessandro K. Jordão, Elis H. S. Ribeiro, Natália R. S. Araújo, Rita C. O. Sebastião & Cícero F. S. Aragão. (2022) Characterization and thermal decomposition kinetic study of promising antioxidante nitroxides. Journal of Thermal Analysis and Calorimetry 147:23, pages 13395-13403.
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Anna C. Cunha, Vitor F. Ferreira, Maria G. F. Vaz, Rafael A. Allão Cassaro, Jackson A. L. C. Resende, Carolina Q. Sacramento, Jéssica Costa, Juliana L. Abrantes, Thiago Moreno L. Souza & Alessandro K. Jordão. (2020) Chemistry and anti-herpes simplex virus type 1 evaluation of 4-substituted-1H-1,2,3-triazole-nitroxyl-linked hybrids. Molecular Diversity 25:4, pages 2035-2043.
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Shengdian Huang, Maren Pink, Thacien Ngendahimana, Suchada Rajca, Gareth R. Eaton, Sandra S. Eaton & Andrzej Rajca. (2021) Bis-Spiro-Oxetane and Bis-Spiro-Tetrahydrofuran Pyrroline Nitroxide Radicals: Synthesis and Electron Spin Relaxation Studies. The Journal of Organic Chemistry 86:19, pages 13636-13643.
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Zhimin Yang, Richard A. Stein, Thacien Ngendahimana, Maren Pink, Suchada Rajca, Gunnar Jeschke, Sandra S. Eaton, Gareth R. Eaton, Hassane S. Mchaourab & Andrzej Rajca. (2020) Supramolecular Approach to Electron Paramagnetic Resonance Distance Measurement of Spin-Labeled Proteins. The Journal of Physical Chemistry B 124:16, pages 3291-3299.
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Hongchang Shi & Yong Li. (2013) Amine-catalyzed olefin epoxidation mechanism with enantioselectivity: Oxidation by secondary amine N,N-dioxo-radical derived from electron spin resonance, electrospray ionization-mass spectrometry and density functional theory calculation. Journal of Molecular Catalysis A: Chemical 374-375, pages 73-84.
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Raphael F. Queiroz, Alessandro K. Jordão, Anna C. Cunha, Vitor F. Ferreira, Maísa R.P.L. Brigagão, Alberto Malvezzi, Antonia T.-do Amaral & Ohara Augusto. (2012) Nitroxides attenuate carrageenan-induced inflammation in rat paws by reducing neutrophil infiltration and the resulting myeloperoxidase-mediated damage. Free Radical Biology and Medicine 53:10, pages 1942-1953.
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Denise A. Souza, Yanko Moreno, Eduardo A. Ponzio, Jackson A.L.C. Resende, Alessandro K. Jordão, Anna C. Cunha, Vitor F. Ferreira, Miguel A. Novak & Maria G.F. Vaz. (2011) Synthesis, crystal structure, magnetism and electrochemical properties of two copper(II) furoyltrifluoroacetonate complexes with nitroxide radical. Inorganica Chimica Acta 370:1, pages 469-473.
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N. B. Mel’nikova, I. V. Gulyaev, M. V. Gulenova, A. A. Volkov, O. E. Zimnyakova, V. P. Gubskaya, L. Sh. Berezhnaya, A. T. Gubaidullin & I. A. Nuretdinov. (2009) Structure of surface films of malonate mono- and dinitroxyl methanofullerenes. Russian Chemical Bulletin 57:9, pages 1955-1966.
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Karen Wright, Laurence Dutot, Michel Wakselman, Jean-Paul Mazaleyrat, Marco Crisma, Fernando Formaggio & Claudio Toniolo. (2008) Synthesis, resolution and assignment of absolute configuration of trans 3-amino-1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic acid (POAC), a cyclic, spin-labelled β-amino acid. Tetrahedron 64:19, pages 4416-4426.
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Valérie Sciannamea, Robert Jérôme & Christophe Detrembleur. (2008) In-Situ Nitroxide-Mediated Radical Polymerization (NMP) Processes:  Their Understanding and Optimization. Chemical Reviews 108:3, pages 1104-1126.
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Karen Wright, Matthieu Sarciaux, Augustin de Castries, Michel Wakselman, Jean‐Paul Mazaleyrat, Antonio Toffoletti, Carlo Corvaja, Marco Crisma, Cristina Peggion, Fernando Formaggio & Claudio Toniolo. (2007) Synthesis of Enantiomerically Pure cis ‐ and trans ‐4‐Amino‐1‐oxyl‐2,2,6,6‐tetramethylpiperidine‐3‐carboxylic Acid: A Spin‐Labelled, Cyclic, Chiral β‐Amino Acid, and 3D‐Structural Analysis of a Doubly Spin‐Labelled β‐Hexapeptide . European Journal of Organic Chemistry 2007:19, pages 3133-3144.
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Hong-Chang Shi & Yong Li. (2007) Formation of nitroxide radicals from secondary amines and peracids: A peroxyl radical oxidation pathway derived from electron spin resonance detection and density functional theory calculation. Journal of Molecular Catalysis A: Chemical 271:1-2, pages 32-41.
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Louis F. Fieser, Mary Fieser & Tse‐Lok HoTse‐Lok Ho, Mary Fieser & Louis Fieser. 2006. Fieser and Fieser's Reagents for Organic Synthesis. Fieser and Fieser's Reagents for Organic Synthesis.
Zhiqiang Liu, M. Francesca Ottaviani, Lloyd Abrams, Xuegong Lei & Nicholas J. Turro. (2004) Characterization of the External Surface of Silicalites Employing Electron Paramagnetic Resonance , . The Journal of Physical Chemistry A 108:39, pages 8040-8047.
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Peter Nesvadba, Lucienne Bugnon & Rosemarie Sift. (2004) New 7‐membered diazepanone alkoxyamines for nitroxide‐mediated radical polymerization. Journal of Polymer Science Part A: Polymer Chemistry 42:13, pages 3332-3341.
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Karen Wright, Marco Crisma, Claudio Toniolo, Roland Török, Antal Péter, Michel Wakselman & Jean-Paul Mazaleyrat. (2003) 4-Amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid (β-TOAC), the first spin-labelled, cyclic, chiral β-amino acid resolved in an enantiomerically pure state. Tetrahedron Letters 44:16, pages 3381-3384.
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Steffen Jockusch, Zhiqiang Liu, M. Francesca Ottaviani & Nicholas J. Turro. (2001) Time Resolved CW-EPR Spectroscopy of Powdered Samples:  Electron Spin Polarization of a Nitroxyl Radical Adsorbed on NaY Zeolite, Generated by the Quenching of Excited Triplet Ketones. The Journal of Physical Chemistry B 105:31, pages 7477-7481.
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Ralph Bågenholm, Ulf A Nilsson, Cecilia Wallin Götborg & Ingemar Kjellmer. (1998) Free Radicals Are Formed in the Brain of Fetal Sheep during Reperfusion after Cerebral Ischemia. Pediatric Research 43:2, pages 271-275.
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Marina Kveder, Greta Pifat, Slavko Pečar, Milan Schara, Pilar Ramos & Hermann Esterbauer. (1997) Nitroxide reduction with ascorbic acid in spin labeled human plasma LDL and VLDL. Chemistry and Physics of Lipids 85:1, pages 1-12.
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B. Poch, F. Gansauge, S. Gansauge, T. Anger, U. Nilsson, M. H. Schoenberg & H. G. Beger. (1996) Release of histamine in whole blood by oxygen radicals: Division between specific and unspecific processes. Inflammation Research 45:8, pages 428-433.
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G. HARALDSSON, V. SORENSEN, U. NILSSON, S. PETTERSSON, M. RASHID, T. SCHERSTÉN, S. ÅKERLUND & O. JONSSON. (2008) Effect of pre‐treatment with desferrioxamine and mannitol on radical production and kidney function after ischaemia‐reperfusion. A study on rabbit kidneys. Acta Physiologica Scandinavica 154:4, pages 461-468.
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Jacques Einhorn, Cathy Einhorn, Fabien Ratajczak & Jean-Louis Pierre. (1995) Synthesis of stable α,α′-bis(carboxymethyl) substituted nitroxides via an original dianion-based strategy. J. Chem. Soc., Chem. Commun.:10, pages 1029-1030.
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Ulf A. Nilsson, Michael H. Schoenberg, Anders Åneman, Bertram Poch, Sunita Magadum, Hans G. Beger & Ove Lundgren. (1994) Free radicals and pathogenesis during ischemia and reperfusion of the cat small intestine. Gastroenterology 106:3, pages 629-636.
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U. A. NILSSON, G. HARALDSSON, S. BRATELL, V. SORENSEN, S. AKERLUND, S. PETTERSSON, T. SCHERSTEN & O. JONSSON. (2008) ESR‐measurement of oxygen radicals in vivo after renal ischaemia in the rabbit. Effects of pre‐treatment with superoxide dismutase and heparin . Acta Physiologica Scandinavica 147:3, pages 263-270.
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G. HARALDSSON, U. NILSSON, S. BRATELL, S. PETTERSSON, T. SCHERSTÉN, S. ÅKERLUND & O. JONSSON. (2008) ESR‐measurement of production of oxygen radicals in vivo before and after renal ischaemia in the rabbit . Acta Physiologica Scandinavica 146:1, pages 99-105.
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