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87413-09-0 - Dess-Martin periodinane - DMP - 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one - L15779 - Alfa Aesar

L15779 Dess-Martin periodinane

CAS-Nummer
87413-09-0
Synonyme
DMP
1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one

Größe Preis ($) Menge Verfügbarkeit
1g 32,45
5g 129,78
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Dess-Martin periodinane

MDL
MFCD00130127

Chemische Eigenschaften

Formel
C13H13IO8
Molmasse
424.15
Schmelzpunkt
130-132° dec.
Sensitivität
Moisture & Light Sensitive
Löslichkeit
Soluble in chloroform, acetone, acetonitrile and methylene chloride. Slightly soluble in ether and hexane.

Anwendungen

Dess Martin periodinane is used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones. It is also used as an oxidant for complexes with multifunctional alcohols. It is actively involved in the oxidation of N-protected-amino alcohols without epimerization and allylic alcohols.

Bemerkungen

Store in cool place. Air and moisture sensitive. Incompatible with strong reducing agents, combustible material and water.

Literaturverweise

One of the mildest reagents for the selective oxidation of primary and secondary alcohols to aldehydes and ketones. High yields can be obtained at ambient temperatures, under neutral conditions, in chloroform, dichloromethane or acetonitrile: J. Org. Chem., 48, 4155 (1983); J. Am. Chem. Soc., 113, 7277 (1991); (reviews): J. Prakt. Chem./ Chem. Ztg., 338, 588 (1996); Synlett, 278 (2000). Has been employed for the oxidation of a wide variety of sensitive substrates and is particularly valuable in multi-step syntheses of polyfunctional molecules with complex stereochemistry. For an example involving exclusive oxidation of one of four possible secondary OH groups in a synthesis of erythromycin B, see: J. Am. Chem. Soc., 119, 3193 (1997). Allylic and benzylic alcohols can be oxidized selectively in the presence of saturated alcohols, and give the carbonyl compounds cleanly without over-oxidation or cis-trans isomerization: Tetrahedron Lett., 29, 995 (1988); J. Org. Chem., 55, 1636 (1990).

Hydroxamic acids are oxidized to acyl nitroso compounds which can undergo cycloaddition to dienes: Synth. Commun., 30, 47 (2000).

Has also been used for deoximation of ketoximes to ketones under mild conditions: Tetrahedron Lett., 39, 3209 (1998); Synthesis, 760 (1999).

For use in the synthesis of imides, N-acyl vinylogous carbamates and ureas, and nitriles, by oxidation of amides and amines, see: Angew. Chem. Int. Ed., 44, 5992 (2005).

Deprotection of thioacetals can be accomplished under extremely mild conditions: Org. Lett., 5, 575 (2003).

ɑ,ß-Unsaturated carboxylic acids undergo Hunsdiecker-type decaboxylative bromination with tetraethylammonium bromide in the presence of the reagent: Synlett, 2495 (2005).

CAUTION! In the presence of moisture, may form iodoxybenzoic acid which has been reported to be explosive under excessive heating or impact: Chem. Eng. News, 68(29), 3 (1990).

For a detailed discussion of the scope and advantages of this reagent, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 7, p. 4982.

Gamapwar, S. V.; Tale, N. P.; Karade, N. N. Dess-Martin Periodinane-Mediated Oxidative Aromatization of 1,3,5-Trisubstituted Pyrazolines. Synth. Commun. 2012, 42 (17), 2617-2623.

Schrockeneder, A.; Stichnoth, D.; Mayer, P.; Trauner, D. The crystal structure of the Dess-Martin periodinane. Beilstein J. Org. Chem. 2012, 8, 1523-1527.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H272-H315-H319-H335

May intensify fire; oxidizer. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Sicherheitshinweise: P221-P210-P220-P261-P280-P305+P351+P338-P304+P340-P362-P405-P501a

Take any precaution to avoid mixing with combustibles. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep/Store away from clothing/combustible materials. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Merck
14,2933
Beilstein
4548207
Gefahrenklasse
5.1
Verpackungsgruppe
III
Harmonized Tariff Code
2934.99
TSCA
No

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