Tetracarbonylferrate, sodium

Sodium reacts with iron pentacarbonyl to produce a salt known as sodium tetracarbonylferrate(—II)2, Na2Fe(CO)4, which has been shown by J. P. Collman and co-workers to have considerable potential as a reagent for organic synthesis. 

Sodium N-methylanilide, 459 Sodium methylsulfinylmethylide, 195-196 Sodium naphthalenide, 349-350 Sodium nitrite, 459-460 Sodium nitrosodisulfonate, 411 Sodium orthophosphate dodecahydrate, 309 Sodium perborate, 59 Sodium phenanthrenide, 375 Sodium phenoxide, 352 Sodium phenoxides, 86 Sodium sulfide, 77,460-461 Sodium sulfite, 91 Sodium tetraborate, 461 Sodium tetracarbonylferrate(-Il), 461-465 Sodium tetraphenylborate, 81 Sodium thiocyanate, 7 Sodium thioethoxide, 465 Sodium thiophenoxide, 314,460 Sodium thiosulfate, 466 Sommelet reaction, 243 Spiroalkylation, 213-214 Spirobutanones, 211-212 Spiro[l,3-dithiol-2,9 -fluorene], 446 Spiro-epoxy-2,4-cyclohexadienones, 373-374... 

ALDEHYDES 9-Borabicyclo[3.3.1]-nonane. Diazoacetaldehyde. Diethyl-allylthiome thylphosphonate, Diethyl phenyl orthoformate Dithiane. Lith-ium-Alkylamine. Lithium diisopropyl-amide. Sodium tetracarbonylferrate-(TI). 1,1,3,3-Tetramethylbutylisonitrile. 2,4,4,6-Tetramethyl-5,6-dihydro-l, 3-(4H)-oxazine. Triethylsilane. s-Trithiane. 

An alternative route to aldehydes from carboxylic acids involves conversion of the acid into the carboxylic ethylcarbonic anhydride (1) by reaction with ethyl chloroformate. These anhydrides react with sodium tetracarbonylferrate... 

ALDEHYDES Bis(4-methylpiperazinyl)aluminum hydride. Di(r) -cyclopentadienyl)-(chloro)hydridozitconium(IV). Dihalobis(triphenylphosphine)paIIadium(H). 7,8-Dimethyl-l,5-dihydro-2,4-benzodithiepin. Grignard reagents. Lithium bis(ethylene-dioxyboryOmethide. 3-Methyl-I-phenyl-2-phospholene. 2-Methyl-2-thiazoline. Methylthioacetic acid. 3-Methylthio-l,4-diphenyl-s-triazium iodide. Sodium meth-oxide. Methylthiomethyl N,N-dimethyldithiocarbamate. Sodium tetracarbonylferrate(II). Tetra-n-butylammonium borohydride. Triethylallyloxysilane. N,4,4-Trimethyl-2-oxazolinium iodide. 

CYCLOHEXYLIDENEACETALDEHYDES Manganese dioxide. CYCLOPENTANONES Magnesium. 1-Phenylthiocyclopropyltriphenylphosphonium fluoroborate. Simmons Smith reagent. Sodium tetracarbonylferrate(-II). CYCLOPENTENONES 3-Benzyl-5-(2-hydroxyethyl)-4-methyl-l,3-thiazolium chloride. Boron trifluoride etherate. Lithium dimethoxyphosphinylmethylide. Silver tetra-fluoroborate. Titanium tetrachloride. Triethyl phosphite. Vinyl triphenylphos-phonium bromide. 

A. SODIUM SALT OF IRON CARBONYL HYDRIDE Sodium Tetracarbonylferrate(-II))... 

Amides. Sodium acyltetracarbonylferrates, derived from sodium tetracarbonylferrate and acid chlorides, react with nitro compounds, both aliphatic and aromatic, to form amides in 70-857o yield. ... 

In contrast to the usually expensive organo transition metal complexes, sodium tetracarbonylferrate(-II) is inexpensive and versatile. E.g. aldehydes and unsym. ketones can be synthesized from halides and tosylates in high yields with this reagent Thallic nitrate converts acetophenones directly into methyl phenylacetates. Where applicable this new method is more convenient than the rather tedious Willgerodt-Kindler reaction... 

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