Dess-Martin periodinane
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| Dess-Martin periodinane | |
|---|---|
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| General | |
| Systematic name | 1,1,1-Triacetoxy-1,1-dihydro- 1,2-benziodoxol-3(1H)-one |
| Other names | Dess-Martin periodinane |
| Molecular formula | C13H13IO8 |
| SMILES | O=C2C1=CC=CC=C1I (OC(C)=O)(OC(C)=O) (OC(C)=O)O2 |
| Molar mass | 424.14 g/mol |
| Appearance | white powder, chips, crystals or crystalline powder and/or chunks |
| CAS number | 87413-09-0 |
| Properties | |
| Density and phase | 1.362 g/cm3 solid |
| Solubility in water | ? g/100 ml (? °C) |
| Melting point | 103 - 133 °C |
| Structure | |
| Crystal structure | ? |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 |
0
1
2
|
| Flash point | ? °C |
| R/S statement | R: R20/21/22, R36/37/38 S: S26, S36 |
| RTECS number | ? |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related compounds | 2-Iodoxybenzoic acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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The Dess-Martin periodinane is a chemical reagent used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones. This periodinane has several advantages over chromium- and DMSO-based oxidants that include milder conditions, shorter reaction times, higher yields, and simplified workups.
Contents |
[edit] Preparation
2-Iodobenzoic acid is oxidized preferably by Oxone, or by KBrO3 to 2-iodoxybenzoic acid. (Caution: 2-Iodoxybenzoic acid has been found to be impact and heat sensitive, decomposing explosively.) The 2-Iodoxybenzoic acid is then treated with a mixture of acetic anhydride, acetic acid and p-toluenesulfonic acid at 80-100 °C for 40 min. The resulted solids can be obtained via filtration and washing with ether.
To avoid the explosive nature of 2-iodoxybenzoic acid, other methods of preparation as well as other periodinanes have been described.
[edit] Properties and uses
Dess-Martin periodinane is mainly used as an oxidant for complex, sensitive and multifunctional alcohols. One of the reason for its effectiveness is due to its high selecivity of hydoxylic group, which allows alcohols to rapidly perform ligand exchange; the first step in the oxidation reaction.
Its effectiveness as an oxidant is also due to its versatility; having a broad scope of being able to convert alcohols to carbonyl derivatives. Its reactions and yield is also known to be clean and high respectively. Work up is also clean and simple. Byproducts from the reaction can be removed easily by precipitation, filtration or chromatography.
[edit] References
- ↑ Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
- ↑ Boeckman, R. J. In "Encyclopedia of Reagents for Organic Synthesis"; Paquette, L. A., Ed.; Wiley: Chichester, UK, 1995, Vol. 7, pp. 4982-4987. (Review)
- ↑ Boeckman, Jr., R. K.; Shao, P.; Mullins, J. J. Organic Syntheses, Coll. Vol. 10, p.696 (2004); Vol. 77, p.141 (2000). (Article)
- ↑ Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
- ↑ Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
- ↑ Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
