Iodosobenzene

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Iodosobenzene
Names
Preferred IUPAC name
Iodosylbenzene[1]
Other names
Iodosobenzene
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.007.864 Edit this at Wikidata
EC Number
  • 208-648-8
UNII
  • InChI=1S/C6H5IO/c8-7-6-4-2-1-3-5-6/h1-5H checkY
    Key: JYJVVHFRSFVEJM-UHFFFAOYSA-N checkY
  • InChI=1/C6H5IO/c8-7-6-4-2-1-3-5-6/h1-5H
    Key: JYJVVHFRSFVEJM-UHFFFAOYAR
  • c1ccc(cc1)I=O
Properties
C6H5IO
Molar mass 220.01 g/mol
Appearance colourless solid
Density 1.229 g cm−3
Melting point 210 ˚C
poor
Hazards
GHS labelling:[2]
GHS02: FlammableGHS03: OxidizingGHS07: Exclamation mark
Danger
H228, H271, H315, H319, H335
P210, P220, P240, P241, P261, P264, P264+P265, P271, P280, P283, P302+P352, P304+P340, P305+P351+P338, P306+P360, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P371+P380+P375, P403+P233, P405, P420, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Iodosobenzene or iodosylbenzene is an

coordination chemistry
.

Preparation and structure

Iodosobenzene is prepared from iodobenzene.[3] It is prepared by first oxidizing iodobenzene by peracetic acid. Hydrolysis of resulting diacetate affords "PhIO":[4]

C6H5I + CH3CO3H + CH3CO2H → C6H5I(O2CCH3)2 + H2O
C6H5I(O2CCH3)2 + H2O → C6H5IO + 2 CH3CO2H

The structure of iodosobenzene has been verified by

vibrational spectroscopy indicate that it is not molecular, but is polymeric, consisting of –I–O–I–O– chains.[7] The related diacetate, C6H5I(O2CCH3)2, illustrates the ability of iodine(III) to adopt a T-shaped geometry without multiple bonds.[8]
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.[9]

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.[10]

Structure of 2-(tert-butylsulfonyl)iodosylbenzene.

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.[11]

A mixture of iodosobenzene and sodium azide in acetic acid converts alkenes to vicinal diazides:.[12][13]

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

  1. ISBN 978-0-85404-182-4
    .
  2. ^ "Iodosylbenzene". pubchem.ncbi.nlm.nih.gov.
  3. doi:10.1002/cber.189202502221
    .
  4. doi:10.15227/orgsyn.043.0060
    .
  5. PMID 27761533
    .
  6. PMID 17569525
    .
  7. doi:10.1002/zaac.19764260206
    .
  8. doi:10.1039/C39940002367
    .
  9. PMID 25045143
    .
  10. PMID 10941012
    .
  11. PMID 22639404
    .
  12. doi:10.1016/S0040-4039(00)84648-1
    .
  13. ISBN 978-0-471-72091-1
    .
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