Organomagnesium compounds reactions with

Reactions of Enamine Salts with OrganometalUc Compounds Organolithium and organomagnesium compounds react with enamine salts to give amines substituted on the ix-carbon atoms. The treatment of. -dehydroquinolizidinium perchlorate (163) with alkylmagnesium halides gives 9-alkylated quinolizidines (164) (252,256). Formation of... 

Grignard Reaction The reaction of an organomagnesium compound, typically with a carbonyl compound to produce an alcohol, although it may be used in other situations. 

Organomagnesium compounds react with imines, prepared from 3-methoxy-2-naphth-aldehydes by a 1.4-addition mechanism. This reaction can be performed with high diastere-oselectivity. The method was applied for the synthesis of optically pure S-tetralones . Vinyhnagnesium bromide reacts as an acceptor with a ketone dimethyl hydrazone zincate 207, yielding a 1,1-bimetallic species, which can be reacted sequentially with two different electrophiles (equations 131 and 132) . The reaction proceeds via a metalla-aza-Claisen rearrangement, where the dimethylhydrazone anion behaves as an aza-allylic system . 

Organomagnesium compounds react with enamine salts to give bases substituted on the a-carbon atom. These reactions may be regarded as an extension of Freund s observations on quaternary quinolinium and isoquinolinium salts. The reaction of hydrastinine with methylmagnesium bromide 318 (Eq. 10) is a typical example. The... 

Oxidative coupling. Organolithium and organomagnesium compounds react with the complex in THF or dimethoxyethane at —78° to give copper(l) ate complexes, which in the presence of atmospheric oxygen undergo coupling.2 The reaction of it-butyllithium is typical ... 

Organohthium and organomagnesium compounds find their chief use m the prepa ration of alcohols by reaction with aldehydes and ketones Before discussing these reac tions let us first examine the reactions of these organometallic compounds with proton donors... 

The term Grignard reaction refers to both the preparation of a class of organomagnesium haUde compounds and their subsequent reaction with a wide variety of organic and inorganic substrates. As such it has had a wide and profound influence on synthetic chemistry since its first elucidation by Victor Grignard at the beginning of the twentieth century. 

Grignard reagent (Section 14.4) An organomagnesium compound of the type RMgX formed by the reaction of magnesium with an alkyl or aryl halide. 

A related cleavage reaction (165 166) occurs on the treatment of isoxazoles with organomagnesium compounds.This reaction considerably hinders the use of the Grignard reaction in the isoxazole series (see Section IV,D) in it the activity of the organo-... 

Under the conditions used for the reductive cleavage of the O—N bond in isoxazoles, a similar reaction readily occurs with isoxa-zolines, e.g. on treatment with organomagnesium compounds and on catalytic hydrogenation.- Hydrogenolysis of the O—N bond (180 181 182 183) was used to elucidate the structure of isoxa-zolones from -ketoesters. -... 

The reaction of Grignard reagents with carbonyl compounds has no direct biological counterpart, because organomagnesium compounds are too... 

The reduction of carbonyl compounds by reaction with hydride reagents (H -) and the Grignard addition by reaction with organomagnesium halides (R - +MgBr) are examples of nucleophilic carbonyl addition reactions. What analogous product do you think might result from reaction of cyanide ion with a ketone ... 

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