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Phencyclidine or phenylcyclohexyl piperidine (PCP), also known in its use as a street drug as angel dust among other names, is a dissociative anesthetic mainly used recreationally for its significant mind-altering effects.
Cyclohexylamine is used as an intermediate in synthesis of other organic compounds. It is the precursor to sulfenamide-based reagents used as accelerators for vulcanization. The amine itself is an effective corrosion inhibitor. It has been used as a flushing aid in the printing ink industry. [5]
The reaction mechanism for this reaction has been demonstrated to proceed through steps similar to those known for palladium catalyzed CC coupling reactions. Steps include oxidative addition of the aryl halide to a Pd(0) species, addition of the amine to the oxidative addition complex, deprotonation followed by reductive elimination .
In one variation called the Darapsky degradation, [19] or Darapsky synthesis, a Curtius rearrangement takes place as one of the steps in the conversion of an α-cyanoester to an amino acid. Hydrazine is used to convert the ester to an acylhydrazine , which is reacted with nitrous acid to give the acyl azide.
Phencyclidine (PCP) is believed to be the first arylcyclohexylamine with recognized anesthetic properties, but several arylcyclohexylamines were described before PCP in the scientific literature, beginning with PCA (1-phenylcyclohexan-1-amine) the synthesis of which was first published in 1907.
The reaction mechanism occurs by initial formation of an iminium ion (2) followed by electrophilic addition at the 3-position, in accordance with the expected nucleophilicity of indoles, to give the spirocycle 3. After migration of the best migrating group, deprotonation gives the product (5). The mechanism of the Pictet–Spengler reaction
The mechanism of the Bamberger rearrangement proceeds from the monoprotonation of N-phenylhydroxylamine 1.N-protonation 2 is favored, but unproductive. O-protonation 3 can form the nitrenium ion 4, which can react with nucleophiles (H 2 O) to form the desired 4-aminophenol 5.
In a variation the reaction of phenols and beta-ketoesters and phosphorus pentoxide yields a chromone.This reaction is called Simonis chromone cyclization. [6] [7] The ketone in the ketoester is activated by P 2 O 5 for reaction with the phenol hydroxyl group first, the ester group in it is then activated for electrophilic attack of the arene.