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Disodium tetracarbonylferrate
Disodium tetracarbonylferrate is the chemical compound with the formula Na2[Fe(CO)4]. This oxygen-sensitive colourless solid is employed in organic synthesis",[1] mainly to synthesise aldehydes.[2] It is commonly used with dioxane complexed to the sodium cation, this dioxane solvate being known as Collman's reagent.[3] The tetracarbonylferrate dianion is tetrahedral.[4] Additional recommended knowledge
SynthesisThe reagent was reported by Cooke in 1970.[5] The current synthesis entails the reduction of a solution of iron pentacarbonyl in tetrahydrofuran by sodium-naphthenide. The efficiency of the synthesis depends on the quality of the iron pentacarbonyl.[1] ReactionsThe reagent was originally described for the conversion of primary alkyl bromides, RBr, to the corresponding aldehydes in a two-step, "one-pot" reaction:[5]
This solution is then treated sequentially with PPh3 and then acetic acid to give the aldehyde, RCHO. Disodium tetracarbonylferrate can be used to convert acid chlorides to aldehydes. As for Cooke’s early discovery, an iron acyl complex undergoes protonolysis to give the aldehyde.
Disodium tetracarbonylferrate reacts with alkyl halides (RX) to produce alkyl complexes:
Such iron alkyls can be converted to the corresponding carboxylic acid and acid halides:
One attraction of these methods is the low cost of the iron carbonyl as well as the fact that the procedures are relatively “green” because the side product is iron-based. References
Further reading
Categories: Carbonyl complexes | Iron compounds | Inorganic carbon compounds |
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Disodium_tetracarbonylferrate". A list of authors is available in Wikipedia. |