Dess-Martin-Periodinan

Structural formula
General
Surname	Dess-Martin-Periodinan
other names	1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3 (1 H ) -one
Molecular formula	C 13 H 13 IO 8
External identifiers / databases
CAS number 87413-09-0 EC number 672-328-8 ECHA InfoCard 100.197.885 PubChem 159087 Wikidata Q420909
properties
Molar mass	424.14 g · mol -1
Physical state	firmly
density	1.36 g cm −3
Melting point	133-134 ° C
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 272-315-319-335 P: 210-220-221-305 + 351 + 338-370 + 378
MAK	not assigned, as a suspected carcinogenic effect
Toxicological data	873 mg kg −1 ( LD 50 ,  mouse ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dess-Martin-Periodinane is a chemical compound that is used in organic synthesis to oxidize primary alcohols to aldehydes and secondary alcohols to ketones . It is named after the American chemists Daniel Benjamin Dess and James Cullen Martin . Compared with oxidizing agents to chromium - or DMSO basis ( Jones - or Swern oxidation ) has Dess-Martin periodinane several advantages. In addition to milder conditions, lower toxicity , shorter reaction times and higher yields, this also includes simpler work-up after the reaction.

synthesis

The synthesis starts from 2-iodobenzoic acid, which is oxidized to IBX (1-hydroxy-1,2-benziodoxol-3 (1 H ) -one-1-oxide) in the first step using potassium bromate . The target molecule is obtained in the second step by acetylation with acetic anhydride and acetic acid .

properties

The connection is thermally unstable. When heated with inclusion to temperatures above 130 ° C, explosive decomposition can occur. In the presence of water or humidity, hydrolysis to IBX takes place.

use

Dess-Martin periodinane, in the Dess-Martin oxidation used.

literature

• Dess, DB. and Martin, JC. (1983): Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones . In: J. Org. Chem. 48 (22), 4155-4156; doi : 10.1021 / jo00170a070
• Dess, DB. and Martin, JC. (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 . In: J. Am. Chem. Soc. 113 (19): 7277-7287; doi : 10.1021 / ja00019a027
• Ireland, RE. and Liu, L. (1993): An improved procedure for the preparation of the Dess-Martin periodinane . In: J. Org. Chem. 58 (10), p. 2899; doi : 10.1021 / jo00062a040 ;
• Meyer, SD. and Schreiber, SL. (1994): Acceleration of the Dess-Martin Oxidation by Water . In: J. Org. Chem. 59 (24), 7549-7552; doi : 10.1021 / jo00103a067
• Boeckman, RJ In " Encyclopedia of Reagents for Organic Synthesis "; Paquette, LA, Ed .; Wiley: Chichester, UK, 1995, Vol. 7, pp. 4982-4987. (Review)
• Boeckman, Jr., RK .; Shao, P .; Mullins, JJ .: The Dess-Martin Periodinane: 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3 (1H) -one In: Organic Syntheses . 77, 2000, p. 141, doi : 10.15227 / orgsyn.077.0141 ; Coll. Vol. 10, 2004, p. 696 ( PDF ).

Web links

Commons : Dess-Martin periodinane  - collection of images, videos and audio files

Individual evidence

1. ↑ ^{a b c} data sheet Dess-Martin periodinane, 15 wt.% Solution in dichloromethane from Acros, accessed on December 1, 2019.
2. ↑ ^{a b c} Dess, DB; Martin, JC: A Useful 12-I-5 Triacetoxyperiodinane (the Dess-Martin Periodinane) for the Selective Oxydation of Primary or Secondary Alcohols and a Variety of Related 12-I-5 Species in J. Am. Chem. Soc. 113 (1991) 7277-72787. doi : 10.1021 / ja00019a027
3. ↑ ^{a b} Data sheet Dess-Martin periodinane, 97% from Sigma-Aldrich , accessed on December 1, 2019 ( PDF ).
4. ↑ DB Dess: JC Martin: Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones in J. Org. Chem. 48 (1983) 4155-4156. doi : 10.1021 / jo00170a070 .
5. ↑ Plumb, JB; Harper, DJ: Chem. Eng. News 1990, 68 (29), 3.