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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.
Acetaldehyde is a common electrophile in organic synthesis. [31] In addition reactions acetaldehyde is prochiral. It is used primarily as a source of the "CH 3 C + H(OH)" synthon in aldol reactions and related condensation reactions. [32] Grignard reagents and organolithium compounds react with MeCHO to give hydroxyethyl derivatives. [33]
The Bodroux–Chichibabin aldehyde synthesis is a chemical reaction whereby a Grignard reagent is converted to an aldehyde one carbon longer. Reaction of a Grignard reagent with triethyl orthoformate gives an acetal, which can be hydrolyzed to an aldehyde. For example, the synthesis of n-hexanal: [1] Bodroux-Chichibabin hexanal [1]
Often cross-coupling reactions require metal catalysts. One important reaction type is this: R−M + R'−X → R−R' + MX (R, R' = organic fragments, usually aryl; M = main group center such as Li or MgX; X = halide) These reactions are used to form carbon–carbon bonds but also carbon-heteroatom bonds.
Akabori amino-acid reaction – The reduction of amino acid esters, by sodium, to yield aldehydes; Birch reduction – For the reduction of alkenes using sodium; Bouveault aldehyde synthesis – Another organometallic reaction by Bouveault where a Grignard reagent is converted to an aldehyde
Proline derivative 3d is prepared in a separate leg from a Grignard reaction with Grignard reagent 3c and proline ester 3b. A Lewis acid superacid salt (6) can be obtained with the aid of triflic acid (5). Many other such catalysts exist with different derivatives of these reactants.
The reaction mechanism [8] of the Bartoli indole synthesis is illustrated below using o-nitrotoluene (1) and propenyl Grignard (2) to form 3,7-dimethylindole (13). The mechanism of the Bartoli indole synthesis. The mechanism begins by the addition of the Grignard reagent (2) onto the nitroarene (1) to form intermediate 3.