Junttila, Mikko H.’s team published research in Journal of Organic Chemistry in 2007-04-13 | CAS: 92093-23-7

Journal of Organic Chemistry published new progress about Acid catalysis. 92093-23-7 belongs to class alcohols-buliding-blocks, name is 1-(4-Bromophenyl)ethane-1,2-diol, and the molecular formula is C8H9BrO2, Safety of 1-(4-Bromophenyl)ethane-1,2-diol.

Junttila, Mikko H. published the artcileOn the Hydrolysis Step in Osmium Catalyzed Asymmetric Dihydroxylations, Safety of 1-(4-Bromophenyl)ethane-1,2-diol, the main research area is hydrolysis osmium catalysis asym dihydroxylation.

In order to obtain information about the most important features that affect the efficiency of osmium catalyzed asym. dihydroxylation, a series of substituted styrenes have been studied by using a Hammett type approach as well as solvent kinetic isotope effects. A concave shaped Hammett plot with a min. at X = H revealed a change in the mechanism going from electron-donating to electron-withdrawing substituents for both NaClO2 and K3[Fe(CN)6] asym. dihydroxylations. The Hammett plot together with solvent isotope effect results indicates that osmium (mono)glycolates of styrenes with electron-withdrawing substituents are hydrolyzed by a stepwise attack of the nucleophile to the electrophilic osmium-center and subsequent protonation of the alk. intermediate. Osmium (mono)glycolates in dihydroxylation, using NaClO2 as the stoichiometric oxidant of styrenes with electron-donating substituents, are hydrolyzed by specific acid catalysis. The rate-limiting step is an A1 type process. Differences in the ρ values in the Hammett plots for NaClO2 and K3[Fe(CN)6] asym. dihydroxylations indicate that in dihydroxylations with NaClO2 as the secondary oxidant, the reactive osmium(VI) mono(glycolate) is oxidized to osmium(VIII) mono(glycolate) prior to hydrolysis. The reaction rate was found to have an effect on the enantioselectivity in asym. dihydroxylation. If the hydrolysis step is slow enough, a competitive bis(glycolation) deteriorates the enantioselectivity in K3[Fe(CN)6] asym. dihydroxylations and even more so in NaClO2 asym. dihydroxylations.

Journal of Organic Chemistry published new progress about Acid catalysis. 92093-23-7 belongs to class alcohols-buliding-blocks, name is 1-(4-Bromophenyl)ethane-1,2-diol, and the molecular formula is C8H9BrO2, Safety of 1-(4-Bromophenyl)ethane-1,2-diol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts