Iodosylbenzene

Moriarty, Robert M.; Kosmeder, Jerome W.; Zhdankin, Viktor V.

doi:10.1002/047084289x.ri039

Cited by 4 publications

(2 citation statements)

References 67 publications

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“…Following literature methods, to a 250 mL flask containing [ 15 N]isobutyramide (8.8 g, 100.0 mmol) in CH 3 CN (150 mL), hydroxy(tosyloxy)iodobenzene (HTIB) was added at room temperature. The solution was refluxed for 3.0 h and cooled to −20 °C overnight.…”

Section: Methodsmentioning

confidence: 99%

Sodium Isopropyl(trimethylsilyl)amide: A Stable and Highly Soluble Lithium Diisopropylamide Mimic

Lui

Keresztes

et al. 2022

J. Org. Chem.

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The preparation, structure, physical properties, and reactivities of sodium isopropyl(trimethylsilyl)amide (NaPTA) are described. The solubilities at room temperature range from n-heptane (0.55 M), n-hexane (0.60 M), toluene (0.65 M), MTBE (1.7 M), Et3N (3.2 M), and THF (>6.0 M). The half-life to destruction in neat THF is >1 year at 25 °C and 7 days at 70 °C, which compares favorably to 2.5 months and 1.5 days, respectively, for LDA in neat THF. This study focuses on NaPTA in THF. 29Si NMR spectroscopy shows exclusively a mixture of cis and trans stereoisomeric dimers in 0.10–12 M THF in hexane. Density functional theory (DFT) computations suggest that the pK b is intermediate between dimeric sodium diisopropylamide (NaDA) and dimeric sodium hexamethyldisilazide (NaHMDS). Metalations of arenes, epoxides, ketones, hydrazones, alkenes, and alkyl halides show higher reactivities than LDA (k NaPTA/LDA = 1–30). While the rates of arene metalation are high, the lower pK b of NaPTA limits the substrates. Metalation of pseudoephedrate-based carboxamides to form disodiated Myers enolates solves several challenging technical problems.

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Section: Methodsmentioning

confidence: 99%

Sodium Isopropyl(trimethylsilyl)amide: A Stable and Highly Soluble Lithium Diisopropylamide Mimic

Lui

Keresztes

et al. 2022

J. Org. Chem.

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“…2 However, the practical use of iodosylbenzene is hampered by its low stability and potentially explosive properties upon moderate heating and insolubility in most solvents as a result of its polymeric structure. 3 Recently, we have reported the preparation, Xray crystal structure, and oxidative properties of oligomeric iodosylbenzene sulfate (PhIO) 3 ·SO 3 (1), which is readily available, water-soluble, and stable iodosylbenzene analogue. 4 Compound 1 can be conveniently prepared in high yield by a solvent-free reaction of (diacetoxyiodo)benzene with sodium bisulfate monohydrate (Equation 1) and isolated as a yellow crystalline product after crystallization from water.…”

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confidence: 99%

Preparation and Reactivity of Polystyrene-Supported Iodosylbenzene Sulfate: An Efficient Recyclable Oxidizing System

Chen¹,

Zeng²,

Zhdankin³

2010

Synlett

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A new polymer-supported hypervalent iodine reagent, polystyrene-supported iodosylbenzene sulfate (PS-IBS), can be conveniently prepared by the reaction of polystyrene-supported (diacetoxyiodo)benzene (PS-DIB) with sodium bisulfate monohydrate under solvent-free conditions. This new recyclable reagent effects clean and efficient oxidation of a wide range of alcohols and sulfides to the corresponding carbonyl compounds or sulfoxides in high conversions under mild conditions. The final products are conveniently separated from the polymeric byproduct by simple filtration and isolated in good purity after evaporation of solvent. Recycling of the resin is possible with minimal loss of activity after several reoxidations.

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Preparation and Structure of Oligomeric Iodosylbenzene Sulfate (PhIO)₃·SO₃: Stable and Water‐Soluble Analog of Iodosylbenzene

et al. 2007

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New phenyliodine(III) sulfate (PhIO)3·SO3, which has a complex polymeric structure of the trimeric iodosylbenzene units linked by sulfate anions, can be conveniently prepared by treatment of (diacetoxy)iodobenzene with sodium bisulfate in the presence of water. This sulfate can find practical application as a readily available, stable, and water‐soluble hypervalent iodine reagent with a reactivity pattern similar tothat of iodosylbenzene. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Iodosylbenzene

Cited by 4 publications

References 67 publications

Sodium Isopropyl(trimethylsilyl)amide: A Stable and Highly Soluble Lithium Diisopropylamide Mimic

Sodium Isopropyl(trimethylsilyl)amide: A Stable and Highly Soluble Lithium Diisopropylamide Mimic

Preparation and Reactivity of Polystyrene-Supported Iodosylbenzene Sulfate: An Efficient Recyclable Oxidizing System

Preparation and Structure of Oligomeric Iodosylbenzene Sulfate (PhIO)₃·SO₃: Stable and Water‐Soluble Analog of Iodosylbenzene

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Iodosylbenzene

Cited by 4 publications

References 67 publications

Sodium Isopropyl(trimethylsilyl)amide: A Stable and Highly Soluble Lithium Diisopropylamide Mimic

Sodium Isopropyl(trimethylsilyl)amide: A Stable and Highly Soluble Lithium Diisopropylamide Mimic

Preparation and Reactivity of Polystyrene-Supported Iodosylbenzene Sulfate: An Efficient Recyclable Oxidizing System

Preparation and Structure of Oligomeric Iodosylbenzene Sulfate (PhIO)3·SO3: Stable and Water‐Soluble Analog of Iodosylbenzene

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Preparation and Structure of Oligomeric Iodosylbenzene Sulfate (PhIO)₃·SO₃: Stable and Water‐Soluble Analog of Iodosylbenzene