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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 6, 1976 - Issue 1
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Original Articles

Lead Tetraacetate Oxidation of Trimethylsilyl Enol Ethers: Synthesis of Aryl Substituted Phenacyl Acetates

G. M. Rubottom Department of Chemistry, University of Idaho, Moscow, Idaho, 83843
,
J. M. Grube Department of Chemistry, University of Idaho, Moscow, Idaho, 83843
&
K. Kincaid Department of Chemistry, University of Idaho, Moscow, Idaho, 83843
Pages 59-62 | Received 05 Oct 1975, Published online: 05 Dec 2006

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S. Munavalli, D. K. Rohrbaugh, D. I. Rossman, W. G. Wagner & H. D. Durst. (2003) Trifluoromethylthiolation of N,O-Bis-(trimethylsilyl)acetamide. Phosphorus, Sulfur, and Silicon and the Related Elements 178:1, pages 107-113.
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Articles from other publishers (28)

Debasish Ghosh, Aniruddha Ganguly & Saikat Khamarui. (2023) Water-based efficient alkyne transformation towards α-acetoxy/imido-ketones via oxidative coupling reactions using an alkylamine catalyst . Organic & Biomolecular Chemistry 21:25, pages 5225-5233.
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Richard C. LarockRichard C. Larock, Anton V. Dubrovskiy & Nataliya A. Markina. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 145 .
Richard C. LarockRichard C. Larock & Tuanli Yao. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 85 .
Feng Zhu & Zhong-Xia Wang. (2014) Bu4NI-catalyzed α-acyloxylation reaction of ethers and ketones with aldehydes and tert-butyl hydroperoxide. Tetrahedron 70:52, pages 9819-9827.
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Tomoaki Hasui, Norio Ohyabu, Taiichi Ohra, Koji Fuji, Takahiro Sugimoto, Jun Fujimoto, Kouhei Asano, Masato Oosawa, Sachiko Shiotani, Nobuhiro Nishigaki, Keiji Kusumoto, Hideki Matsui, Atsushi Mizukami, Noriyuki Habuka, Satoshi Sogabe, Satoshi Endo, Midori Ono, Christopher S. Siedem, Tony P. Tang, Cassandra Gauthier, Lisa A. De Meese, Steven A. Boyd & Shoji Fukumoto. (2014) Discovery of 6-[5-(4-fluorophenyl)-3-methyl-pyrazol-4-yl]-benzoxazin-3-one derivatives as novel selective nonsteroidal mineralocorticoid receptor antagonists. Bioorganic & Medicinal Chemistry 22:19, pages 5428-5445.
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Zheng-Wang Chen, Dong-Nai Ye, Min Ye & Liang-Xian Liu. (2013) Palladium-catalyzed Oxidation of Benzyl Ketones to Synthesis of α-Acetoxy Ketones Using Molecular Oxygen. Chemistry Letters 42:11, pages 1388-1390.
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Guisheng Deng & Jing Luo. (2013) Silver(I)-catalyzed reaction of terminal alkynes with (diacetoxyiodo)benzene: a convenient, efficient and clean preparation of α-acetoxy ketones. Tetrahedron 69:29, pages 5937-5944.
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Xerardo García-Mera, Maria J. Alves, Albertino Goth, Maria Luísa do Vale & José E. Rodríguez-Borges. (2013) Highly stereoselective cycloadditions of Danishefsky's diene to (−)-8-phenylmenthyl and (+)-8-phenylneomenthyl glyoxylate N-phenylethylimines. Tetrahedron 69:14, pages 2909-2919.
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Dong-Liang Mo, Li-Xin Dai & Xue-Long Hou. (2009) The reaction of terminal alkynes with PhI(OAc)2: a convenient procedure for the preparation of α-acyloxy ketones. Tetrahedron Letters 50:40, pages 5578-5581.
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Louis F. Fieser, Mary Fieser & Tse‐Lok HoTse‐Lok Ho, Mary Fieser, Louis Fieser, Rick Danheiser, William Roush & Janice Smith. 2006. Fieser and Fieser's Reagents for Organic Synthesis. Fieser and Fieser's Reagents for Organic Synthesis.
Robert M. Moriarty. (2005) Organohypervalent Iodine:  Development, Applications, and Future Directions. The Journal of Organic Chemistry 70:8, pages 2893-2903.
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Bang‐Chi Chen, Ping Zhou, Franklin A. Davis & Engelbert Ciganek. 2004. Organic Reactions. Organic Reactions 1 356 .
Norio Ohyabu, Toshio Nishikawa & Minoru Isobe. (2003) First Asymmetric Total Synthesis of Tetrodotoxin. Journal of the American Chemical Society 125:29, pages 8798-8805.
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Robert M. Moriarty & Om Prakash. 2004. Organic Reactions. Organic Reactions 273 418 .
Sandrine Piguel, Gerardo Ulibarri & David S. Grierson. (1999) Studies toward the construction of the allyltrisulfide component in esperamicin-A1 from 5-ketoshikimic acid derivatives: Part 2. Tetrahedron Letters 40:2, pages 295-298.
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. 1998. Ligand Coupling Reactions with Heteroatomic Compounds. Ligand Coupling Reactions with Heteroatomic Compounds 205 247 .
Martine M.L. Crilley, David S. Larsen, Richard J. Stoodley & Fernando Tom?. (1993) Unusual allylic acetoxylations of silyl enol ethers with lead(IV) acetate. Tetrahedron Letters 34:20, pages 3305-3308.
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Robert M. Moriarty, Bruce A. Berglund & Raju Penmasta. (1992) Direct ?-hydroxylation of ketones under acidic conditions using [bis (trifluoroacetoxy)] iodobenzene. Tetrahedron Letters 33:41, pages 6065-6068.
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David J. Ager & Michael B. East. (1992) Methodology to establish 1,2- and 1,3-difunctionality for the synthesis of carbohydrate derivates. Tetrahedron 48:14, pages 2803-2894.
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Robert M. Moriarty, Raju Penmasta & Indra Prakash. (1987) Synthesis of 1,4-diketones by the coupling reaction of trimethylsilyl enol ethers with lead tetraacetate. Tetrahedron Letters 28:8, pages 873-876.
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Seijiro Matsubara, Kazuhiko Takai & Hitosi Nozaki. (1983) Baeyer-Villiger Oxidation with Me3SiOOSiMe3 under Assistance of SnCl4 or BF3·OEt2. Bulletin of the Chemical Society of Japan 56:7, pages 2029-2032.
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George M. Rubottom, Roberto Marrero & John M. Gruber. (1983) The reaction of aldehyde enol silyl ethers with lead(IV) acetate. Tetrahedron 39:6, pages 861-865.
Crossref
William P. WeberWilliam P. Weber. 1983. Silicon Reagents for Organic Synthesis. Silicon Reagents for Organic Synthesis 228 234 .
GEORGE M. RUBOTTOM. 1982. Oxidation in Organic Chemistry, Part D. Oxidation in Organic Chemistry, Part D 1 145 .
Ernest W. Colvin. 1981. Silicon in Organic Synthesis. Silicon in Organic Synthesis 198 287 .
Ingolf Dyong & Norbert Jersch. (2006) Synthesen biologisch wichtiger Kohlenhydrate, 18. Die vic. cis ‐Oxyaminierung als Schlüsselreaktion für Aminozucker‐Synthesen: Methyl‐ N ‐acety‐4‐epi‐α‐garosaminid . Chemische Berichte 112:5, pages 1849-1858.
Crossref
. 1978. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 336 495 .
G. M. RUBOTTOM, J. M. GRUBER & K. KINCAID. (2016) ChemInform Abstract: LEAD TETRAACETATE OXIDATION OF TRIMETHYLSILYL ENOL ETHERS‐ SYNTHESIS OF ARYL SUBSTITUTED PHENACYL ACETATES. Chemischer Informationsdienst 7:24.
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