31527-84-1

Upstream product

• 74806-54-5 cis-4,5-Dimethyl-cyclohexene Epoxide 
• 113348-84-8 (+)-trans-8-thiabicyclo<4.3.0>nonan-3-one 
• 203319-65-7 (1R,2R)-1,2-Dimethyl-cyclohexane 

Downstream Products

• 113348-79-1 (+)-(3S,4S)-3,4-dimethylcyclohexanone 

Relevant academic research and scientific papers

Oxidative functional group transformations with hydrogen peroxide catalyzed by a divanadium-substituted phosphotungstate

A divanadium-substituted phosphotungstate TBA4[γ-PW 10O38V2(μ-OH)(μ-O)] (I, TBA = tetra-n-butylammonium) reacts with one equivalent H+ to form a bis-μ-hydroxo species [γ-PW10O38V 2(μ-OH)2]3- (I′) in organic media. The strong electrophilic oxidants such as [γ-PW10O 38V2(μ-OH)(μ-OOH)]3- (II) and [γ-PW10O38V2(μ-η2: η2-O2)]3- (III) are formed by the reaction of the bis-μ-hydroxo species with H2O2. In the presence of I and H+, H2O2-based oxidations such as (i) epoxidation of alkenes (17 examples including electron-deficient ones), (ii) hydroxylation of alkanes (11 examples), and (iii) oxidative bromination of alkenes, alkynes, and aromatics with Br- as a bromo source (12 examples including chlorination) chemo-, diastereo-, and regioselectively proceed to give the corresponding oxidized products in moderate to high yields with high efficiencies of H2O2 utilization.

Enzymes in Organic Synthesis. 41. Stereoselective Horse Liver Alcohol Dehydrogenase Catalyzed Reductions of Heterocyclic Bicyclic Ketones

Preparative-scale horse liver alcohol dehydrogenase catalyzed reductions of racemic cis and trans bicyclic O- and S-heterocyclic ketones proceed with high enantiomeric selectivity.The diastereotopic selectivity for the pro-R faces of the carbonyl groups is also very high.The ee's of all but one of the product alcohols are >97percent.The ee's of the recovered ketones are in the 52-60percent range.The results confirm that an ether-oxygen or -sulfur substituent does not alter the enzyme's overall structural specificity or stereospecificity toward its ketone substrates.

Mechanism of the Liquid-Phase Catalytic Hydrogenolysis on Palladium/Carbon of Cyclohexene Epoxides

Heterogeneous catalytic hydrogenolysis of cyclohexene epoxides on 10percent Pd/C was studied in different solvents. The principal products were found to be alcohols, formed by cleavage of one epoxide C-O bond. In addition, simultaneous cleavage of both C-O bonds gave hydrocarbons, and isomerization on the catalyst gave ketones as byproducts. The deuterolysis of cis- and trans-tert-butylcyclohexene epoxides and kinetic studies with cyclohexene epoxides carrying an axial methyl group in position 3 or 5 showed that hydrogenolysis gives preferentially axial alcohols and trans hydrogen addition, after a "roll over" on the catalyst. If one epoxide carbon carries a methyl group, conformational and steric factors come into play. C-O bond cleavage at the more substituted carbon, leading to equatorial alcohols, becomes competitive with preferential formation of axial alcohols, and steric hindrance to molecular reorientation on the catalyst causes cis as well as trans hydrogen addition.