ORGN 395 |
SIBX: a new stabilized o-iodoxybenzoic acid formulation as a mild and selective oxidizing system
| Aurélie Ozanne1, Laurent Pouységu1, Dominique Depernet2, and Stéphane Quideau1. (1) Institut Européen de Chimie et Biologie, Université Bordeaux 1, Pessac, France, (2) Simafex, 16 Avenue des Fours-à-Chaux, 17230 Marans, France, 16 Avenue des Fours-à-Chaux, Marans, France |
SIBX, standing for Stabilized IBX, is a non-explosive, non-moisture sensitive and non-toxic formulation of the l5-iodane o-iodoxybenzoic acid (IBX) composed of carboxylic acidic stabilizing agents such as benzoic and isophtalic acids. SIBX-mediated oxidations were successfully carried out on a series of alcohols in several solvent systems, generating only 2-iodosobenzoic acid as an insoluble and recyclable by-product. Application of this hypervalent iodine-based reagent to the ortho-selective oxygenation of various arenols led to orthoquinones and/or dimerizing orthoquinol derivatives depending on the substitution pattern of the starting arenols. Exploitation of this latter reaction for the synthesis of bioactive natural products will be presented. |
| |
|
Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
|