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The Ireland–Claisen rearrangement is the reaction of an allylic carboxylate with a strong base (such as lithium diisopropylamide) to give a γ,δ-unsaturated carboxylic acid. [ 25 ] [ 26 ] [ 27 ] The rearrangement proceeds via silylketene acetal, which is formed by trapping the lithium enolate with chlorotrimethylsilane.
claisen-condensation. RSC ontology ID. RXNO:0000043. The Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base. The reaction produces a β-keto ester or a β- diketone. [1] It is named after Rainer Ludwig Claisen, who first ...
A 1,2-rearrangement is an organic reaction where a substituent moves from one atom to another atom in a chemical compound. In a 1,2 shift the movement involves two adjacent atoms but moves over larger distances are possible. Skeletal isomerization is not normally encountered in the laboratory, but is the basis of large applications in oil ...
The Dieckmann condensation is the intramolecular chemical reaction of diesters with base to give β-keto esters. [1] It is named after the German chemist Walter Dieckmann (1869–1925). [2][3] The equivalent intermolecular reaction is the Claisen condensation. Dieckmann condensations are highly effective routes to 5-, 6-, and 7-member rings ...
Crossover experiment (chemistry) In chemistry, a crossover experiment is a method used to study the mechanism of a chemical reaction. In a crossover experiment, two similar but distinguishable reactants simultaneously undergo a reaction as part of the same reaction mixture. The products formed will either correspond directly to one of the two ...
Oxymercuration reaction. In organic chemistry, the oxymercuration reaction is an electrophilic addition reaction that transforms an alkene (R2C=CR2) into a neutral alcohol. In oxymercuration, the alkene reacts with mercuric acetate (AcO−Hg−OAc) in aqueous solution to yield the addition of an acetoxymercury (−HgOAc) group and a hydroxy ...
The Hofmann rearrangement (Hofmann degradation) is the organic reaction of a primary amide to a primary amine with one less carbon atom. [1][2][3] The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate. The reaction can form a wide range of products, including ...
The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann (1853–1923), is a rearrangement of an oxime functional group to substituted amides. [ 1 ][ 2 ] The rearrangement has also been successfully performed on haloimines and nitrones. Cyclic oximes and haloimines yield lactams.