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The Wolff–Kishner reduction is a reaction used in organic chemistry to convert carbonyl functionalities into methylene groups. [1] [2] In the context of complex molecule synthesis, it is most frequently employed to remove a carbonyl group after it has served its synthetic purpose of activating an intermediate in a preceding step.
Acetophenone is formed as a byproduct of the cumene process, the industrial route for the synthesis of phenol and acetone.In the Hock rearrangement of isopropylbenzene hydroperoxide, migration of a methyl group rather than the phenyl group gives acetophenone and methanol as a result of an alternate rearrangement of the intermediate:
When derived from hydrazine itself, hydrazones condense with a second equivalent of a carbonyl to give azines: [11] R 2 C=N−NH 2 + R 2 C=O → R 2 C=N−N=CR 2 + H 2 O. Hydrazones are intermediates in the Wolff–Kishner reduction. Hydrazones are reactants in hydrazone iodination, the Shapiro reaction, and the Bamford–Stevens reaction to ...
The Fischer indole synthesis is a chemical reaction that produces the aromatic heterocycle indole from a (substituted) phenylhydrazine and an aldehyde or ketone under acidic conditions. [1] [2] The reaction was discovered in 1883 by Emil Fischer. Today antimigraine drugs of the triptan class are often synthesized by this method. The Fischer ...
Acetone hydrazone can be produced on large scale by reaction of acetone azine with hydrazine, a more convenient reaction than direct reaction of acetone and hydrazine. [3] Likewise, it is susceptible to disproportionation to revert to acetone azine and hydrazine, especially in the presence of water.
Tosylhydrazone salts can react with metals to form metal carbenes and used in cyclopropanations and epoxidations. [ 3 ] [ 4 ] An example of a transition metal - catalyzed cyclopropanation is a synthesis of tranylcypromine , [ 5 ] [ 6 ] in which the sodium salt of benzaldehyde tosylhydrazone is converted to a rhodium metal carbene through the ...
This reaction is, overall, a condensation reaction as two molecules joining together with loss of water. Mechanistically, it is an example of addition-elimination reaction: nucleophilic addition of the -NH 2 group to the C=O carbonyl group, followed by the elimination of a H 2 O molecule: [3] X-ray structure of DNP-derived hydrazone of ...
The initial product is a thioamide for example that of acetophenone [7] which can again be hydrolyzed to the amide. The reaction is named after Karl Kindler The Kindler modification of the Willgerodt rearrangement. A possible reaction mechanism for the Kindler variation is depicted below: [8] The likely reaction mechanism for the Kindler ...