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Carbon-metal bond formation acyl halides

It is known that insertion of carbon monoxide to form an acyl complex is reversible, in which results depend on the pressure of carbon monoxide and temperature. If the above-mentioned mechanisms are correct, then acyl halides and aldehydes should be decarbonylated to form olefins provided that an acyl-palladium bond is formed by the oxidative addition of acyl halides or aldehydes to metallic palladium. This proved to be the case. When acyl halide was heated with a catalytic amount of metallic palladium or palladium chloride at 200°C. in a distilling flask, carbon monoxide and hydrogen halide were evolved rapidly, and olefin was collected in a good yield. This reaction is a new and useful preparative method of olefins. In the same way, aldehydes can be decarbonylated smoothly, but in this case, both olefin and the corresponding paraffin Were obtained. The latter probably arises by the hydrogenation of the olefin. Decarbonylation of certain aldehydes has been reported by several workers (3, 6), but no reasonable mechanism has been known. The mechanism of the palladium-catalyzed aldehyde formation discussed above gives clear explanation for the palladium catalyzed decarbonylation of aldehydes. [Pg.160]


See other pages where Carbon-metal bond formation acyl halides is mentioned: [Pg.5647]    [Pg.5646]    [Pg.1115]    [Pg.1115]    [Pg.164]    [Pg.204]    [Pg.152]    [Pg.439]    [Pg.439]    [Pg.188]    [Pg.439]    [Pg.329]    [Pg.135]    [Pg.92]    [Pg.95]    [Pg.52]    [Pg.324]    [Pg.520]    [Pg.520]    [Pg.221]   
See also in sourсe #XX -- [ Pg.1110 , Pg.1114 ]




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Acyl halides formation

Acyl metalate

Acyl-metal bond

Acylal formation

Acylals formation

Bonding carbon-metal bond

Bonds acyl halides

Bonds carbon metal

Bonds carbon-metal bond

Carbon halides

Carbon-metal bond formation

Carbon-metal bonds acyl halides

Formates, acylation

Formates, metalated

Halide bond

Halides formation

Metal acyl halides

Metal formate

Metal halide formation

Metals, formation

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