The Barbier reaction is an organic reaction between a alkyl halide and a carbonyl group as an electrophilic substrate in the presence of aluminium, zinc, indium, tin or its salts. The reaction product is a secondary or tertiary alcohol. The reaction is similar to the Grignard reaction but the crucial difference is that the Barbier reaction is a One-pot synthesis whereas a Grignard reagent is prepared separately before addition of the carbonyl compound ¹. Barbier reactions are nucleophilic addition reactions that take place with relatively inexpensive and water insensitive metals or metal compounds in contrast to Grignard reagents or organolithium reagents. For this reason it is possible in many cases to run the reaction in water which makes the procedure part of green chemistry. The Barbier reaction is named after Victor Grignard’s teacher Oliver Barbier. Organic reactions are chemical reactions between organic compounds. ... In chemistry, an alkyl halide is an organic molecule of the form R_X, where X is a halide and R contains a carbon atom bonded to other functional groups or hydrogens. ... In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom. ... In chemistry, an electrophile (literally electron-lover) is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to bond to a substance. ... Jump to: navigation, search General Name, Symbol, Number aluminium, Al, 13 Chemical series poor metals Group, Period, Block 13, 3, p Appearance silvery Atomic mass 26. ... Jump to: navigation, search General Name, Symbol, Number zinc, Zn, 30 Chemical series transition metals Group, Period, Block 12, 4, d Appearance bluish pale gray Atomic mass 65. ... Jump to: navigation, search General Name, Symbol, Number indium, In, 49 Chemical series poor metals Group, Period, Block 13, 5, p Appearance silvery lustrous gray Atomic mass 114. ... Jump to: navigation, search General Name, Symbol, Number tin, Sn, 50 Chemical series poor metals Group, Period, Block 14, 5, p Appearance silvery lustrous gray Atomic mass 118. ... Jump to: navigation, search In general usage, alcohol (from Arabic al-ghawl الغول) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... A Grignard Reagent is an alkyl- or aryl- magnesium halide. ... In chemistry a one-pot synthesis is a strategy with the aim to improve the effiency of a chemical reaction whereby a reactant is subjected to successive chemical reactions in one and the same reactor. ... In organic chemistry, a nucleophilic addition reaction is an addition reaction where in a chemical compound a pi bond is removed by the creation of two new covalent bonds by the addition of a nucleophile. ... An organolithium reagent is any organic compound with a direct bond between a carbon and a lithium atom. ... Green Chemistry is the design of chemical products and processes that reduce or eliminate the use and generation of hazardous substances. ... François Auguste Victor Grignard (born in Cherbourg, 6 May 1871, died in Lyon, 13 December 1935) was a Nobel Prize-winning French chemist. ... Jump to: navigation, search Oliver Barbier is currently Chair Executive Officer of one of the nations most prestigious corporations, Selvok Pharmaceutical Company. ...

Examples of Barbier reactions are the reaction of propargylic bromide with butanal with zinc metal in water ²,

the intramolecular Barbier reaction with samarium(II) iodide ³, Jump to: navigation, search Image File history File links Barbier1. ... Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms. ... Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms. ... Propyl allene is the simplest allene. ... Intramolecular describes a process or characteristic limited within the structure of a single, or each molecule; a property or phenomenon limited to the extent of a single, or each molecule. ... Samarium(II) iodide (SmI2) is a green solid composed of samarium and iodine, with a melting point of 520 °C [1]. It can be formed by high temperature decomposition of SmI3 (the more stable iodide), but a convenient lab preparation is to react Sm powder with 1,2-diiodoethane in...

the reaction of an allyl bromide with formaldehyde in THF with indium powder ⁴, Jump to: navigation, search Image File history File links Barbier2. ... An allyl group is an alkene hydrocarbon group with the formula H2C=CH-CH2-. It is made up of a vinyl group, CH2=CH-, attached to a methylene -CH2. ... The chemical compound formaldehyde (also known as methanal), is a gas with a strong pungent smell. ... Jump to: navigation, search General Name, Symbol, Number indium, In, 49 Chemical series poor metals Group, Period, Block 13, 5, p Appearance silvery lustrous gray Atomic mass 114. ...

or another allyl bromide in a reaction with benzaldehyde and zinc powder in water ⁵. Jump to: navigation, search Image File history File links Barbier3. ... The chemical compound benzaldehyde (C6H5CHO) consists of a benzene ring with an aldehyde group attached to one carbon. ... Jump to: navigation, search General Name, Symbol, Number zinc, Zn, 30 Chemical series transition metals Group, Period, Block 12, 4, d Appearance bluish pale gray Atomic mass 65. ...

Jump to: navigation, search Image File history File links Barbier4. ... Jump to: navigation, search Diastereomers are stereoisomers that are not enantiomers or mirror images of each other. ... Diastereomers are stereoisomers that are not enantiomers or mirror images of each other. ... Diastereomers are stereoisomers that are not enantiomers or mirror images of each other. ...

External links

• Barbier reaction @ University of Connecticut Website

University of Connecticut The University of Connecticut, commonly known as UConn, is the State of Connecticuts flagship land-grant university. ...

References

• ¹ Barbier, P. Compt. Rend., 1899, 128, 110.
• ² Zn Mediated Regioselective Barbier Reaction of Propargylic Bromides in THF/aq. NH4Cl Solution Artur Jõgi and Uno Mäeorg Molecules 2001, 6, 964-968 Article
• ³ Preparation of oxo-substituted α-chloro ethers and their reaction with samarium diiodide Tore Skjæret and Tore Benneche Arkivoc KU-242A 2001 Article
• ⁴ Methyl 3-(hydroxymethyl)-4-methyl-2-methylenepentanoate George D. Bennett and Leo A. Paquette Organic Syntheses, Coll. Vol. 10, p.541; Vol. 77, p.107
• ⁵ Use of Cyclic Allylic Bromides in the Zinc–Mediated Aqueous Barbier–Grignard ReactionGary W. Breton, John H. Shugart, Christine A. Hughey, Brian P. Conrad, Suzanne M. Perala Molecules 2001, 6, 655-662 Article