Iodobenzene diacetate – Wikipedia

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Iodobenzene diacetate
Image illustrative de l’article Diacétate d'iodobenzène
Identification
UICPA name bis (acetyloxy) (phenyl) -λ 3 -Iodane
Synonyms
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Iodosobenzene diacetate
phenylioDiacetate
(Diacetoxyiodo) Benzene
Ask

N O CAS 3240-34-4
N O Echa 100.019.826
N O THIS 221-808-1
N O RTECS DA3525000
Pubchem 76724
SMILES
Inches
Chemicals
Formula C ten H 11 It 4 [Isomers]
Molar mass [ first ] 322.096 4 ± 0.01 G/MOL
C 37,29 %, H 3,44 %, I 39,4 %, O 19,87 %,
Physical properties
T° fusion 161-163 °C [ 2 ]
Precautions
Directive 67/548/EEC [ 2 ] , [ 3 ]
Nocif
Xn
Irritant
Xi
Ecotoxicology
DL 50 56 mg · kg -first (mouse, i.v.) [ 4 ]
IS units and CNTP , unless otherwise stated.
modifier Consultez la documentation du modèle

The iodobenzene diacetate , (Diacetoxyiodo) Benzene , Phenyliod diacetate or Ask (from English P henyl I leather D i A ceteate ), is a periodinan, an organic compound hypervalent of iodine (iii) (iodinane λ 3 ).

It is possible to prepare it by oxidation of iodobenzene by peracetic acid and acetic acid [ 5 ] :

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C 6 H 5 I + CH3COOOH + CH3COOH → C6H5I(OCOCH3)2 + H2O,

Iodobenzene diacetate is a versatile chemical reagent, mainly used as an oxidant. It can, for example, be used to oxidize alcohols [ 6 ] or in the aziridination of alkenes with sulfamates, catalyzed by rhodium [ 2 ] . In fact, this reagent is useful for the synthesis of a wide variety of heterocyclical compounds [ 2 ] .

Iodobenzene diacetate is also used in the synthesis of 5 or 6 links from β-hydroxyethers and γ-hydroxyethers via a photochemical route [ 7 ] .

This photochemical reaction has been used many times in order to synthesize natural products. [ 8 ]

It is also used to cleave glycols and α-hydroxycetones in cycle opening reactions and Mannich’s reaction.

It can also be hydrolyzed in iodoxybenzene (iodylbenzene) C 6 H 5 O 2 I [ 9 ] , or even in iodosobenzene in the presence of sodium hydroxide [ ten ] .

  1. ↑ Molar mass calculated after ‘ Atomic weights of the elements 2007 » , on www.chem.qmul.ac.uk .
  2. ↑ A B C and D (Diacetoxyiodo)benzene chez Sigma-Aldrich.
  3. ↑ Iodobenzene Diacetate At TCI Europe.
  4. ↑ (in) ‘ Iodobenzene diacetate » , on Chedplus .
  5. ↑ J. G. Sharefkin and H. Saltzman, Benzene, iodoso-, diacetate , Org. Synth., coll.  « vol. 5 », p. 660
  6. ↑ G. Piancatelli, F. Leonelli, Oxidation of nerol to neral with iodobenzene diacetate et TEMPO , Org. Synth., 2006, vol. 83, p. 18.
  7. ↑ (in) Kyoji Furuta , TAKUSHI Nagata et Hisashi Yamamoto , ‘ A direct synthesis of cyclic acetals from β- or γ-hydroxy ethersby means of C-H activation » , Tetrahedron Letters , vol. 29, n O 18, , p. 2215–2218 (DOI  10.1016/S0040-4039(00)86715-5 , read online , consulted the )
  8. ↑ (in) Jonathan Sperry , Yen-Cheng (William) Liu and Margaret A. Brimble , ‘ Synthesis of natural products containing spiroketals via intramolecular hydrogen abstraction » , Org. Biomol. Chem. , vol. 8, n O 1, , p. 29–38 (ISSN  1477-0520 And 1477-0539 , DOI  10.1039/B916041H , read online , consulted the )
  9. ↑ J. G. Sharefkin and H. Saltzman, Benzene, iodoxy- , Org. Synth., coll.  « vol. 5 », p. 665
  10. ↑ H. Saltzman and J. G. Sharefkin, Benzene, iodoso- , Org. Synth., coll.  « vol. 5 », p. 658

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