33928-29-9Relevant 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.
Novel Syntheses of Decacyclene by Deoxygenating Cyclotrimerisation of Acenaphthenequinone with Zero-valent Titanium or Phosphorus Pentasulfide
Zimmermann, Klaus,Haenel, Matthias W.
, p. 609 - 611 (2007/10/03)
Decacyclene (2) was obtained in 15-21% yield by reaction of acenaphthenequinone (6) with bis(η6-biphenyl)titanium(0) (9) in toluene or diglyme at 110°C and in 18% yield by reaction of 6 with phosphorus pentasulfide in boiling toluene. The new reactions are used to attempt the conversion of 3,8-dibromoacenaphthenequinone (7) to 3,4,9,10,15,16-hexabromodecacyclene (3) which is considered to serve as a suitable precursor for the bowl-shaped polycyclic aromatic hydrocarbon C 36H12 (1).
