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| Dess-Martin periodinane | |
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| IUPAC name | 1,1,1-Triacetoxy-1,1-dihydro- 1,2-benziodoxol-3(1H)-one |
| Other names | Dess-Martin periodinane |
| Identifiers | |
| CAS number | [87413-09-0] |
| SMILES |
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| Properties | |
| Molecular formula | C13H13IO8 |
| Molar mass | 424.14 g/mol |
| Appearance | white powder, chips, crystals or crystalline powder and/or chunks |
| Density | 1.362 g/cm3 solid |
| Melting point |
103 - 133 °C |
| 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 references |
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Dess-Martin periodinane is a chemical reagent used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones.[1][2] This periodinane has several advantages over chromium- and DMSO-based oxidants that include milder conditions, shorter reaction times, higher yields, and simplified workups. It is named after the American chemists Daniel Benjamin Dess and James Cullen Martin.
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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.) [3] 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[4][5] as well as other periodinanes[6] have been described.
Properties and uses
Dess-Martin periodinane is mainly used as an oxidant for complex, sensitive and multifunctional alcohols. One of the reasons for its effectiveness is its high selectivity towards complexation of the hydroxylic 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 are 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.
References
- ^ Dess, D. B.; Martin, J. C. (1983). "Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones". J. Org. Chem. 48: 4155. doi:.
- ^ 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. (2004). "The Dess-Martin Periodinane". Org. Synth.; Coll. Vol. 10: 696.
- ^ Ireland, R. E.; Liu, L. (1993). "An improved procedure for the preparation of the Dess-Martin periodinane". J. Org. Chem. 58: 2899. doi:.
- ^ Meyer, S. D.; Schreiber, S. L. (1994). "Acceleration of the Dess-Martin Oxidation by Water". J. Org. Chem. 59: 7549. doi:.
- ^ Dess, D. B.; Martin, J. C. (1991). "A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species". J. Am. Chem. Soc. 113: 7277. doi:.
See also
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- This page was last modified on 21 August 2008, at 18:19.
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