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The Beckmann rearrangement scheme for acetophenone oxime under oxonium–acetic acid complex and hydronium–water complex. With the cyclohexanone-oxime, the relief of ring strain results in a third reaction mechanism, leading directly to the protonated caprolactam in a single concerted step without the intermediate formation of a π-complex or ...
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:
In organic chemistry, an oxime is an organic compound belonging to the imines, with the general formula RR’C=N−OH, where R is an organic side-chain and R' may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds.
After a short synthesis to obtain the desired spiro-[5.4] system, Nobel laureaute E.J. Corey and co-workers employed a Barton reaction to selectively introduce an oxime in a 1,3-diaxial position to the nitrite ester. The oxime is converted to a lactam via a Beckmann rearrangement and then reduced to the natural product. [24]
The Knorr pyrrole synthesis is a widely used chemical reaction that synthesizes substituted pyrroles (3). [ 1 ] [ 2 ] [ 3 ] The method involves the reaction of an α- amino - ketone (1) and a compound containing an electron-withdrawing group (e.g. an ester as shown) α to a carbonyl group (2) .
Acetone oxime (acetoxime) is the organic compound with the formula (CH 3) 2 CNOH. It is the simplest example of a ketoxime. It is a white crystalline solid that is soluble in water, ethanol, ether, chloroform, and ligroin. It is used as a reagent in organic synthesis. [2]
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An example of this reaction is the synthesis of 1-phenylethylamine from acetophenone: [14] Reductive amination acetophenone ammonia. Additionally, many systems catalyze reductive aminations with hydrogenation catalysts. [15]