66622-43-3Relevant academic research and scientific papers
Oxidative cleavage of vicinal diols: IBX can do what Dess-Martin periodinane (DMP) can
Moorthy, Jarugu Narasimha,Singhal, Nidhi,Senapati, Kalyan
, p. 767 - 771 (2008/03/27)
A study was conducted to demonstrate the similarity of reactivity between o-iodoxybenzoic acid (IBX), an oxidative agent of vicinal diols and Des-Martin periodinane (DMP). The study examined IBX-mediated oxidative cleavage of tert,tert-1,2-diols and discovered pathways that favored fragmentation of sec,sec-1,2-diols, which produce non-cleavage products. It was observed that IBX can be employed to perform oxidative cleavage of 1,2-diols similar to DMP by simple variation of solvent and temperature. It was also observed that protonation of 10-1-4 species of diols may suppress the nucleophilic attack, leading to the production of ketol to achieve oxidative cleavage of sec,sec-1,2-diols that yield non-cleavage products with IBX in DMSO. TFA was used as a significant source of protons and a better solvent of IBX to conduct protonation of diols. A variety of sec,sec,tert,tert and sec,tert syn-1,2-diols underwent oxidative cleavage effectively, using TFA as a solvent.
Photo-Fries reaction in water made selective with a capsule
Kaanumalle, Lakshmi S.,Gibb, Corinne L. D.,Gibb, Bruce C.,Ramamurthy
, p. 236 - 238 (2008/03/14)
The water soluble capsule formed by a deep cavity cavitand with eight carboxylic acid groups controls product distribution during photo-Fries rearrangement of naphthyl esters in water by restricting the mobility of primary singlet radical pair. The Royal Society of Chemistry.
