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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 10
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Original Articles

Oxidative Cleavage of Ketoximes with Iodosobenzene Diacetate

Robert M. Moriarty Department of Chemistry, University of Illinois at Chicago, P.O. Box 4348, Chicago, Illinois, 60680
,
Om Prakash Department of Chemistry, University of Illinois at Chicago, P.O. Box 4348, Chicago, Illinois, 60680
&
Pushpa R. Vavilikolanu Department of Chemistry, University of Illinois at Chicago, P.O. Box 4348, Chicago, Illinois, 60680
Pages 1247-1253 | Published online: 05 Dec 2006

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MartinG. Kociolek & Olivia Hoermann. (2012) Synthesis of 1,2-Benzisoxazole 2-Oxides. Synthetic Communications 42:17, pages 2632-2638.
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F. Shirini, M. A. Zolfigol, M. Khaleghi & I. Mohammadpour-Baltork. (2003) Silica Chloride/Wet SiO2 as a Novel Heterogeneous System for Deprotection of Oximes, Hydrazones, and Semicarbazones. Synthetic Communications 33:11, pages 1839-1844.
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F. Shirini, M. A. Zolfigol & A. Pourhabib. (2002) EFFICIENT CLEAVAGE OF CARBON–NITROGEN DOUBLE BONDS UNDER SOLVENT FREE CONDITIONS. Synthetic Communications 32:18, pages 2837-2841.
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Da-Jun Chen, Dong-Ping Cheng & Zhen-Chu Chen. (2001) HYPERVALENT IODINE IN SYNTHESIS. 61. REGENERATION OF CARBONYL FUNCTION FROM CARBONYL DERIVATIVES USING POLYMER-SUPPORTED PHENYLIODINE BIS(TRIFLUOROACETATE). Synthetic Communications 31:24, pages 3847-3850.
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Gui-Sheng Zhang & Bing Chai. (2000) An Efficient, Selective and Inexpensive Supported Oxidant for the Regeneration of Carbonyl Compounds from Oximes, Semicarbazones, 4-Phenylsemicarbazones, and P-Nitrophenylhydrazones. Synthetic Communications 30:10, pages 1849-1855.
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Fener Chen, Anchang Liu, Qiongjiao Yan, Mingxing Liu, Daoming Zhang & Lanying Shao. (1999) Tetrabutylammonium Peroxydisulfate in Organic Synthesis; IV.1 An Efficient, Highly Selective and Oxidative Deoximation by Tetrabutylammonium Peroxydisulfate. Synthetic Communications 29:6, pages 1049-1056.
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Gui-Sheng Zhang, De-Hong Yang & Mi-Feng Chen. (1998) TRIMETHYLAMMONIUM CHLOROCHROMATE (TMACC) ADSORBED ON ALUMINA FOR CLEAVAGE OF CARBON-NITROGEN DOUBLE BONDS UNDER NON-AQUEOUS CONDITIONS. Organic Preparations and Procedures International 30:6, pages 713-716.
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B.P. Bandgar, S.I. Shaikh & Suresh Iyer. (1996) Oxidative Deoximation with Sodium Perborate1 . Synthetic Communications 26:6, pages 1163-1168.
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Latika Singh & RamN. Ram. (1993) Deoximation of Oximes, Sodium Oximates, and O-Benzoyloximes with Copper (II) Chloride Dihydrate. Synthetic Communications 23:22, pages 3139-3147.
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Roman Balicki & Lukasz Kaczmarek. (1991) Mild Reductive Deoximation with TiCl4/NaI Reagent System. Synthetic Communications 21:17, pages 1777-1782.
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N. Chidambaram, K. Satyanarayana & S. Chandrasekaran. (1989) An Efficient and Highly Selective Method for Deoximation of Ketoximes. Synthetic Communications 19:9-10, pages 1727-1734.
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M. Mujahid Alam, Hari Babu Bollikolla, Mohammed Amanullah, Mohamed Hussein & Ravi Varala. (2023) Phenyliodine(III)diacetate (PIDA): Applications in Rearrangement/Migration Reactions. Current Organic Chemistry 27:2, pages 93-107.
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Tomohiro Maegawa, Ryohei Oishi, Ayumi Maekawa, Kazutoshi Segi, Hiromi Hamamoto, Akira Nakamura & Yasuyoshi Miki. (2022) The Reaction of Ketoximes with Hypervalent Iodine Reagents: Beckmann Rearrangement and Hydrolysis to Ketones. Synthesis 54:18, pages 4095-4103.
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Danqing Zheng, Stefanie Plöger, Constantin G. Daniliuc & Armido Studer. (2021) Photo‐Mediated Intermolecular Coupling of Alkenes with Ketones via Acyloxy Nitroso Compounds. Angewandte Chemie International Edition 60:15, pages 8547-8551.
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Danqing Zheng, Stefanie Plöger, Constantin G. Daniliuc & Armido Studer. (2021) Licht‐vermittelte intermolekulare Kupplung von Alkenen mit Ketonen über Acyloxy‐Nitroso‐Verbindungen. Angewandte Chemie 133:15, pages 8629-8634.
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Anastassia Matviitsuk, Mark D. GreenhalghJames E. Taylor, Xuan B. Nguyen, David B. Cordes, Alexandra M. Z. SlawinDavid W. Lupton & Andrew D. Smith. (2019) Unanticipated Silyl Transfer in Enantioselective α,β-Unsaturated Acyl Ammonium Catalysis Using Silyl Nitronates. Organic Letters 22:1, pages 335-339.
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Jean Le Bras & Jacques Muzart. (2018) C-O Bonds from Pd-Catalyzed C(sp 3 )-H Reactions Mediated by Heteroatomic Groups . European Journal of Organic Chemistry 2018:10, pages 1176-1203.
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E. Ramakrishna, Kapil Dev, Saransh Wales Maurya, Ibadur Rahman Siddiqui & Rakesh Maurya. (2017) Hypervalent iodine (III)-mediated oxidation of aryl sulfonylhydrazones: A facile synthesis of N-aroyl-N′-acyl arylsulfonylhydrazides. Tetrahedron Letters 58:6, pages 570-573.
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Rajesh Kumar, Manoj Kumar & Om Prakash. (2016) A Simple and Efficient Method for the Synthesis of Novel Pyrazolyl Isoxazoline Derivatives Using Hypervalent Iodine (III) Reagent. Heteroatom Chemistry 27:4, pages 228-234.
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Sichang Wang, Zhangqin Ni, Yanjie Wang, Yihui Pang & Yuanjiang Pan. (2014) Highly selective acetoxylation of sulfonamides via using phenyliodine(III) diacetate. Tetrahedron 70:38, pages 6879-6884.
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Deepak K. Aneja, Pooja Ranjan, Loveena Arora & Om Prakash. (2014) [Hydroxy(tosyloxy)iodo]benzene-mediated regeneration of carbonyl compounds by cleavage of carbon nitrogen double bonds. Comptes Rendus Chimie 17:9, pages 881-889.
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Hailing Li, Didier Gori, Cyrille Kouklovsky & Guillaume Vincent. (2010) New chiral amino acid-derived α-acyloxynitroso reagents for asymmetric nitroso Diels–Alder reactions. Tetrahedron: Asymmetry 21:11-12, pages 1507-1510.
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Géraldine Calvet, Susannah C. Coote, Nicolas Blanchard & Cyrille Kouklovsky. (2010) α-Acyloxynitroso dienophiles in [4+2] hetero Diels–Alder cycloadditions: mechanistic insights. Tetrahedron 66:16, pages 2969-2980.
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Sharon R. Neufeldt & Melanie S. Sanford. (2009) O -Acetyl Oximes as Transformable Directing Groups for Pd-Catalyzed C−H Bond Functionalization . Organic Letters 12:3, pages 532-535.
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Harisadhan Ghosh & Bhisma K. Patel. (2010) Hypervalent iodine( iii )-mediated oxidation of aldoximes to N-acetoxy or N-hydroxy amides . Org. Biomol. Chem. 8:2, pages 384-390.
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Kewei Wang, Xiaolan Fu, Jinying Liu, Yongjiu Liang & Dewen Dong. (2009) PIFA-Mediated Oxidative Cyclization of 1-Carbamoyl-1-oximylcycloalkanes: Synthesis of Spiro-Fused Pyrazolin-5-one N -Oxides . Organic Letters 11:4, pages 1015-1018.
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. (2005) Tungstate Sulfuric Acid (TSA)/NaNO 2 as a Novel Heterogeneous System for Rapid Deoximation . Bulletin of the Korean Chemical Society 26:9, pages 1431-1433.
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Ardeshir Khazaei, Abbas Amini Manesh & Amin Rostami. (2019) A Mild and Selective Method for the Conversion of Oximes into Ketones and Aldehydes by the Use of N -Bromophthalimide . Journal of Chemical Research 2004:10, pages 695-696.
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Surya K. De & Asok K. Mallik. (1998) An easy construction of 8,12-dioxa-13-azatricyclo[8.3.1.02,7]tetradeca-2(7),3,5,13-tetraen-14-ones. Tetrahedron Letters 39:16, pages 2389-2390.
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Anastasios Varvoglis. (1997) Chemical transformations induced by hypervalent iodine reagents. Tetrahedron 53:4, pages 1179-1255.
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L. Bencharif, A. Tallec & R. Tardivel. (1997) Anodic behaviour of aromatic oximes: an electrochemical deoximation reaction. Electrochimica Acta 42:23-24, pages 3509-3512.
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A. Varvoglis. 1997. Hypervalent Iodine in Organic Synthesis. Hypervalent Iodine in Organic Synthesis 19 50 .
Jitender Mohan Khurana, Abhijit Ray & Prabhat Kumar Sahoo. (1994) Oxidative Deoximation with Sodium Hypochlorite. Bulletin of the Chemical Society of Japan 67:4, pages 1091-1093.
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Anil Wali, Pralhad A. Ganeshpure & Sheo Satish. (1993) Potassium Permanganate Oxidation of Ketone Oximes. A Deprotective Version. Bulletin of the Chemical Society of Japan 66:6, pages 1847-1848.
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R. M. MORIARTY, O. PRAKASH & P. R. VAVILIKOLANU. (2016) ChemInform Abstract: Oxidative Cleavage of Ketoximes with Iodosobenzene Diacetate.. Chemischer Informationsdienst 17:51.
Crossref

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