34882-18-3Relevant academic research and scientific papers
Regio-and stereoselective hydroxybromination and dibromination of olefins using ammonium bromide and oxone
MacHarla, Arun Kumar,Chozhiyath Nappunni, Rohitha,Nama, Narender
supporting information; experimental part, p. 1401 - 1405 (2012/04/04)
An efficient protocol for the synthesis of vicinal bromohydrins and dibromides from olefins is presented. Various olefins are regio-and stereoselectively hydroxybrominated and dibrominated with anti fashion, following Markonikov's rule, using eco-friendly, non-toxic, and stable reagents such as NH4Br and oxone in CH3CN/H2O (1:1) and CH3CN without employing catalyst in moderate to excellent yields. Bromohydrins are formed instantaneously.
Comparative study of the vicinal functionalization of olefins with 2:1 bromide/bromate and iodide/iodate reagents
Agrawal, Manoj K.,Adimurthy, Subbarayappa,Ganguly, Bishwajit,Ghosh, Pushpito K.
supporting information; experimental part, p. 2791 - 2797 (2009/08/08)
A comparative evaluation was made on the syntheses of vicinal halohydrins, halo methyl ethers, and halo acetates from olefins using 2:1 Br-/BrO3- and I-/IO3- reagents. In many cases both reagents afforded products selectively in high yields. The highest halogen atom efficiencies attained were 97% and 93% for Br-/BrO3- and I-/IO3-, respectively. Of the two reagents, I-/IO3- was established to be the preferred reagent for vicinal functionalization of linear alkenes and also for halo acetate preparation. However, only Br-/BrO3- was effective for vicinal functionalization of trans-stilbene and chalcones.
Towards the development of oxadiazinanones as chiral auxiliaries: synthesis and application of N3-haloacetyloxadiazinanones
Hoover, Trisha R.,Groeper, Jonathan A.,Parrott II, Raleigh W.,Chandrashekar, Seshanand P.,Finefield, Jennifer M.,Dominguez, Alexandro,Hitchcock, Shawn R.
, p. 1831 - 1841 (2007/10/03)
Oxadiazinanones derived from (1R,2S)-ephedrine and (1R,2S)-norephedrine were employed in the asymmetric α-halo aldol reaction. The optimized yields and diastereoselectivities for the ephedrine based oxadiazinanone aldol reaction ranged from fair to good.
Towards the development of oxadiazinanones as chiral auxiliaries: synthesis and application of N3-haloacetyloxadiazinanones
Hoover, Trisha R.,Groeper, Jonathan A.,Parrott II, Raleigh W.,Chandrashekar, Seshanand P.,Finefield, Jennifer M.,Dominguez, Alexandro,Hitchcock, Shawn R.
, p. 1831 - 1841 (2022/06/02)
Oxadiazinanones derived from (1R,2S)-ephedrine and (1R,2S)-norephedrine were employed in the asymmetric α-halo aldol reaction. The optimized yields and diastereoselectivities for the ephedrine based oxadiazinanone aldol reaction ranged from fair to good.
Synthesis of bromo- And iodohydrins from deactivated alkenes by use of N-Bromo- and W-iodosaccharin
Urankar, Damijana,Rutar, Irena,Modec, Barbara,Dolenc, Darko
, p. 2349 - 2353 (2007/10/03)
N-Bromo and N-iodosaccharin react with electron-deficient alkenes such as α,β-unsaturated ketones, acids, esters and nitriles in aqueous organic solvents, yielding the corresponding halohydrins in good yields. The reactions take place at room temperature,
Kinetics and mechanism of in situ bromohydroxylation of cinnamic acids by sodium bromate-sodium bisulphite reagent in aqueous acetonitrile medium
Viroopakshappa,Jagannadham
, p. 374 - 377 (2007/10/03)
Rates of bromohydroxylation of 4-substituted cinnamic acids with HOBr, produced in situ from sodium bromate-sodium bisulphite reagent have been studied in aqueous acetonitirile medium iodometrically. Thermodynamic parameters for the adduct formation step
