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The use of hydrogen peroxide as an oxidant would be advantageous, making the reaction more environmentally friendly as the sole byproduct is water. [7] Benzeneseleninic acid derivatives as catalysts have been reported to give high selectivity with hydrogen peroxide as the oxidant. [ 25 ]
Elimination reaction of cyclohexanol to cyclohexene with sulfuric acid and heat [1] An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. [2] The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction ...
The mechanism of nucleophilic epoxidation begins with conjugate addition of the peroxide (or other O-nucleophilic species) to the enone. Metal ions or conjugate acids present in solution coordinate both the peroxide oxygen and the enolate oxygen. Attack of the enolate on the peroxide oxygen generates the epoxide product and releases a leaving ...
The Juliá–Colonna epoxidation is an asymmetric poly-leucine catalyzed nucleophilic epoxidation of electron deficient olefins in a triphasic system.The reaction was reported by Sebastian Juliá at the Chemical Institute of Sarriá in 1980, [1] with further elaboration by both Juliá and Stefano Colonna (Istituto di Chimica Industriale dell'Università, Milan, Italy).
Thermolysis converts 1 to (E,E) geometric isomer 2, but 3 to (E,Z) isomer 4.. The Woodward–Hoffmann rules (or the pericyclic selection rules) [1] are a set of rules devised by Robert Burns Woodward and Roald Hoffmann to rationalize or predict certain aspects of the stereochemistry and activation energy of pericyclic reactions, an important class of reactions in organic chemistry.
The Dakin oxidation (or Dakin reaction) is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide (H 2 O 2) in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidised, whereas the H 2 O 2 is reduced.
Reactions where the stereochemistry of the hydroxyl group is inverted saw lower regioselectivity, and removal of the hydroxyl group gave the exclusive formation of the other regioisomer. It is likely that the close proximity of the hydroxyl group in the syn isomer acidifies the ring-fusion proton through hydrogen-bonding interactions, thus ...
The stereochemistry of the reaction is quite sensitive. Depending on the mechanism of the reaction and the geometry of the alkene starting material, cis and/or trans epoxide diastereomers may be formed. In addition, if there are other stereocenters present in the starting material, they can influence the stereochemistry of the epoxidation.