Acid halides reactions with organometallic

Nitriles are similar in some respects to carboxylic acids and are prepared either by SN2 reaction of an alkyl halide with cyanide ion or by dehydration of an amide. Nitriles undergo nucleophilic addition to the polar C=N bond in the same way that carbonyl compounds do. The most important reactions of nitriles are their hydrolysis to carboxylic acids, reduction to primary amines, and reaction with organometallic reagents to yield ketones. 

Furthermore reactions with difluorophosphoric anhydride are of some importance (55). The easy cleavage of the P—0—P-bridge in reactions with organometallic oxides (17) and halides (18) leads to derivatives of difluorophosphoric acid in a very mild way ... 

Perfluoroalkyl or -aryl halides undergo oxidative addition with metal vapors to form nonsolvated fluonnated organometallic halides and this topic has been die subject of a review [289] Pentafluorophenyl halides react with Rieke nickel, cobalt, and iron to give bispentafluorophenylmetal compounds, which can be isolated in good yields as liquid complexes [290] Rieke nickel can also be used to promote the reaction of pentafluorophenyl halides with acid halides [297] (equation 193)... 

II c., Cl 0 M L- X c Reaction of acyl halides or other acid derivatives with organometallic compounds... 

OTHER ORGANOMETALLIC REAGENTS (see also Carbonylation, Fluorination, Reformatsky reaction) with acids and acyl derivatives with acid halides Benzylchlorobis(triphenyl-phosphine)palladium(II), 30 Cadmium, 60... 

Acetyl ligands, in niobium complexes, C-H BDEs, 1, 298 Achiral phosphines, on polymer-supported peptides, 12, 698 Acid halides, indium compound reactions, 9, 683 Acidity, one-electron oxidized metal hydrides, 1, 294 Acid leaching, in organometallic stability studies, 12, 612 Acid-platinum rf-monoalkynes, interactions, 8, 641 Acrylate, polymerization with aluminum catalysts, 3, 280 Acrylic monomers, lanthanide-catalyzed polymerization,... 

The stereodefined alkenyl halides are of prime importance due to the recent developments of di- or trisubstituted alkene synthesis by cross-coupling reactions between organometallics and alkenyl halides catalyzed by transition metal compounds 171). These alkenyl halides can be conveniently obtained from alkenylboranes or alkeneboronic acids. B-Alk enylcatecholboranes undergo rapid hydrolysis when stirred with excess water at 25 °C (Eq. 109)102). The alkeneboronic acids are usually crystalline solids of low solubility in water and can be easily isolated and handled in air without significant deterioration. 

Another, mechanistically closely related reaction is the cross-coupling reaction of aryl, benzyl, vinyl, or allyl halides with organometallic coupling reactions, such as Grignard reagents or, preferably, less reducing organometallics such as tin compounds or boronic acids RB(OH)2 the latter allow the reaction to be conducted even in aqueous media.83 The principal reaction steps are ... 

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