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    • Iodosobenzene or iodosylbenzene is an organoiodine compound with the empirical formula C6H5IO. This colourless solid compound is used as an oxo transfer reagent in research laboratories examining organic and coordination chemistry.


    Preparation and structure


    Iodosobenzene is prepared from iodobenzene. It is prepared by first oxidizing iodobenzene by peracetic acid. Hydrolysis of resulting diacetate affords "PhIO":

    C6H5I + CH3CO3H + CH3CO2H → C6H5I(O2CCH3)2 + H2O
    C6H5I(O2CCH3)2 + H2O → C6H5IO + 2 CH3CO2H
    The structure of iodosobenzene has been verified by crystallographically. Related derivatives are also oligomeric. Its low solubility in most solvents and vibrational spectroscopy indicate that it is not molecular, but is polymeric, consisting of –I–O–I–O– chains. The related diacetate, C6H5I(O2CCH3)2, illustrates the ability of iodine(III) to adopt a T-shaped geometry without multiple bonds.
    Theoretical studies show that the bonding between the iodine and oxygen atoms in iodosobenzene represents a single dative I-O sigma bond, confirming the absence of the double I=O bond.
    A monomeric derivative iodosylbenzene is known in the form of 2-(tert-butylsulfonyl)iodosylbenzene, a yellow solid. C-I-O angle is 94.78°, C-I and I-O distances are 2.128 and 1.848 Å.


    Applications


    Iodosobenzene has no commercial uses, but in the laboratory it is employed as an "oxo-transfer reagent." It epoxidizes certain alkenes and converts some metal complexes into the corresponding oxo derivatives. Although it is an oxidant, it is also mildly nucleophilic. These oxo-transfer reactions operate by the intermediacy of adducts PhI=O→M, which release PhI.
    A mixture of iodosobenzene and sodium azide in acetic acid converts alkenes to vicinal diazides:.

    R2C=CR2 + 2 NaN3 + PhIO + 2 AcOH → (N3)R2C−CR2(N3) + PhI + 2 AcONa + H2O


    Safety


    This compound is explosive and should not be heated under vacuum.


    See also


    Dess-Martin reagent


    References

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Artikel Terkait "iodosobenzene"

Iodosobenzene - Wikipedia

Iodosobenzene or iodosylbenzene is an organoiodine compound with the empirical formula C6H5IO. This colourless solid compound is used as an oxo transfer reagent in research laboratories examining organic and coordination chemistry.

Iodosobenzene | C6H5IO | CID 92125 - PubChem

Iodosobenzene | C6H5IO | CID 92125 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.

Iodosobenzene - an overview | ScienceDirect Topics

Iodosobenzene, 3-iodosobenzoic acid and 3-chloroperbenzoic acid as well as the well-known oxidant, cumene hydroperoxide, can substitute for NADPH and molecular oxygen in microsomal monoxygenations.

Iodosobenzene - an overview | ScienceDirect Topics

Iodosylbenzene converts cyclic tertiary amines into lactams, 37 as indicated by nicotine affording a 20% yield of cotinine and N -methylpyrrolidine being converted into the corresponding lactam in 55% yield. Vijay Satam, ... Hari Pati, in Tetrahedron, 2010.

Iodosobenzene - an overview | ScienceDirect Topics

Several researchers have devoted efforts toward the development of efficient protocols (especially for the preparation of morphine and galanthamine). 155 Gaunt and co-workers were able to identify iodosobenzene diacetate as an efficient reagent to achieve the desired goal and tricyclic cyclohexadienone 275 was obtained on multi-gram scale. 156 ...

Iodosobenzene | C6H5IO - ChemSpider

ChemSpider record containing structure, synonyms, properties, vendors and database links for Iodosobenzene, 536-80-1, 208-648-8, JYJVVHFRSFVEJM-UHFFFAOYSA-N

Recent Advances in Iodosobenzene‐Mediated Construction of …

20 Des 2017 · Iodosobenzene (PhIO) is a well-known hypervalent iodine reagent for its Lewis acidic oxidizing capability. In recent times it has been repeatedly proven to be a powerful tool for the development of toxic, costly transition-metal-free advanced and impressive methodologies to construct diverse array of different heterocycles.

Iodosobenzene | 536-80-1 - ChemicalBook

18 Des 2024 · Iodosobenzene is used as an oxidizing and acetoxylating agent in organic synthesis. It is actively involved in the preparation of (Z)-3,7-dimethyl-2,6-octadien-1-al (neral) from (Z)-3,7-dimethyl-2,6-octadien-1-ol (nerol) in presence of 2,2,6,6-tetramethylpiperidin-1 …

Organic Syntheses Procedure

Iodosobenzene has been prepared by the action of sodium or potassium hydroxide solution on iodobenzene dichloride 3, 4 and by addition of water to the dichloride. 5

Organic Syntheses Procedure

The crude wet iodosobenzene may also be used directly for the preparation of diphenyliodonium iodide (p. 355), but it is desirable to assay the wet product by titration to determine the quantity of iodoxybenzene needed.