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In organic chemistry, the Bruylants reaction (sometimes misspelled Bruylant) is a substitution reaction in which a Grignard reagent replaces a nitrile on a carbon that also has an amino group. It is useful for synthesizing phenylcyclidine and related dissociative anesthetics .
A solution of a carbonyl compound is added to a Grignard reagent. (See gallery) An example of a Grignard reaction (R 2 or R 3 could be hydrogen). The Grignard reaction (French:) is an organometallic chemical reaction in which, according to the classical definition, carbon alkyl, allyl, vinyl, or aryl magnesium halides (Grignard reagent) are added to the carbonyl groups of either an aldehyde or ...
Grignard reagents or Grignard compounds are chemical compounds with the general formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH 3 and phenylmagnesium bromide (C 6 H 5)−Mg−Br. They are a subclass of the organomagnesium compounds.
hydrolysis of a nitrile to form an amide or a carboxylic acid; organozinc nucleophiles in the Blaise reaction; alcohols in the Pinner reaction. the (same) nitrile α-carbon in the Thorpe reaction. The intramolecular version is called the Thorpe–Ziegler reaction. Grignard reagents to form imines. [5]
Note that if a Grignard reagent (such as RMgBr) is used, the reaction with an enone would instead proceed through a 1,2-addition. The 1,4-addition mechanism of cuprates to enones goes through the nucleophilic addition of the Cu(I) species at the beta-carbon of the alkene to form a Cu(III) intermediate, followed by reductive elimination of Cu(I ...
Goldberg reaction; Gomberg–Bachmann reaction; Gomberg–Bachmann–Hey reaction; Gomberg radical reaction; Gould–Jacobs reaction; Graebe–Ullmann synthesis; Grignard degradation; Griesbaum coozonolysis; Grignard reaction; Grob fragmentation; Grubbs' catalyst in Olefin metathesis; Grundmann aldehyde synthesis; Gryszkiewicz–Trochimowski ...
Ortho esters can be prepared by the Pinner reaction, in which nitriles react with alcohols in the presence of one equivalent of hydrogen chloride. The reaction proceeds by formation of imido ester hydrochloride: RCN + R ′ OH + HCl → [RC(OR ′)=NH 2] + Cl −. Upon standing in the presence of excess alcohol, this intermediate converts to ...
The compound exhibits many reactions typical of aryl bromides. Bromide can be displaced by cyanide to give the nitrile. It forms a Grignard reagent [2] and organolithium compound. 1-Lithionaphthalene can be further lithiated to give 1,8-dilithionaphthalene, a precursor to peri-naphthalene compounds.