Iron pentacarbonyl deoxygenation

A further notable development is the finding that 3-phenyl- and 3-dimethyl-amino-1,2,-dihydropentalene enter into reaction with iron pentacarbonyl in refluxing deoxygenated methylcyclohexane to give (octahapto-l-R-pentalene-ju-carbon-yl)-tetracarbonyldiiron complexes.260 The spectral data for these substances are consistent with either formulation 184 or 185. Under these conditions, dihydro-... 

Deoxygeuation of N-oxides. Amine oxides are deoxygenated to the corresponding amines by reaction with iron pentacarbonyl in boiling di-n-butyl ether. ... 

Sodium (cyclopentadienyl)dicarbonylferrate, dicobaltoctacarbonyl, and iron pentacarbonyl have been reported to deoxygenate epoxides efficiently to the corresponding alkenes. The reaction with (cyclopentadienyl)dicarbonylfeirate proceeds with inversion of stereochemistry, whereas Fe(CO)5 shows low stereoselectivity. Both Co2(CO)8 and Fe(CO)s are applicable to epoxides having carbonyl groups (equations 45 and 46). 

Sulfides. Sulfoxides are deoxygenated to give sulfides when heated with iron pentacarbonyl in diglyme or di-n-butyl ether in fair to excellent yields (50-95%).2... 

DEOXYGENATION Hexachlorodisilane. Iron pentacarbonyl. Sulfur trioxide—Pyridine. 

Lower valent tungsten halides are a new class of deoxygenation agents, e.g. for the conversion of carbonyl or epoxy compounds into olefins . A new reagent, generated in situ from iron pentacarbonyl and a small amount of base in moist solvents, selectively and efficiently hydrogenates the ethylenic portion of a,/ -unsaturated carbonyl compounds, such as ketones or lactones, under mild conditions. Aliphatic tert. amides can be easily reduced to alcohols by alkali metals in hexa-methylphosphoramide and a protic cosolvent such as tert-butanol. Aldehydes can be obtained from acids by catalytic reduction of intermediate carboxylic alkoxyformic anhydrides . Sec. nitro compds. are converted into ketones by the joint action of a nitrite ester and NaNOg under mild, non-acidic conditions . 

Iron pentacarbonyl is a useful reagent for deoxygenating aUphatic, aromatic, and heterocyclic N-oxides (Alper and Edward, 1970). The reaction occurs in the presence of olefin, lactam, and alkoxy functionalities as well as water (as a hydrate). Azoxybenzenes can be reduced to azo compounds, and nitrones to Schiff bases, using this reagent. These reactions may take place by nucleophilic attack of the oxide at a terminal carbonyl carbon to give a dipolar intermediate (XXXV), which can then collapse to the deoxygenated... 

Iron pentacarbonyl is an excellent reagent for deoxygenating dialkyl, diaryl, or heterocyclic sulfoxides to sulfides (Alper and Keung, 1970). The mechanism for this reaction is similar to that described for the N-oxide-Fe(CO)5 reaction. Moderate yields of thiobenzophenones were realized by reaction of diaryl sulfines with Fc2(CO)9 in benzene or Mn2(CO)io in heptane (Alper, 1975b). a-Bromo sulfoxides (XL) react with Mo(CO)g in 1,2-dimethoxyethane to... 

Hexafluoroazomethane has been converted into the corresponding azine (CFarN-NiCFj) by heating it with iron pentacarbonyl at 190 °C the same paper describes the deoxygenation of hexafiuoroazoxymefhane with... 

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