Carbanion addition to a metalated acetaldehyde. A new regiospecific alkene synthesis

The reaction of 2-[(dicarbonyl)(η 5-cyclopentadienyl)iron]acetaldehyde with organolithium and Grignard reagents results in efficient addition to the aldehyde carbonyl. The intermediate alkoxides have been treated with tetrafluoroboric acid to give high yields of isolated η 2-alkene complexes of the...

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Bibliographic Details
Published inJournal of organometallic chemistry Vol. 322; no. 1; pp. 99 - 102
Main Authors Marten, David F., Akbari, Mahmoud N.
Format Journal Article
LanguageEnglish
Published LAUSANNE 1 Elsevier B.V 17.03.1987
Elsevier
Elsevier Science
Subjects
Aliphatic compounds
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
Cationic complex
Hydrocarbon
Aliphatic compound
Organic ligand
Transition metal Carbonyl Complexes
Carbanion
1,3-Butadiene
Ligand reaction
Regiospecificity
Iron Carbonyl Complexes
Grignard reagent
Styrene
Conjugated dienic compound
Hapto complex
Ethylenic compound
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Summary:The reaction of 2-[(dicarbonyl)(η 5-cyclopentadienyl)iron]acetaldehyde with organolithium and Grignard reagents results in efficient addition to the aldehyde carbonyl. The intermediate alkoxides have been treated with tetrafluoroboric acid to give high yields of isolated η 2-alkene complexes of the dicarbonyl(η 5-cyclopentadienyl)iron cation. Using this procedure the following alkenes were produced as complexed ligands to iron in 50–90% yield: propene, 1-hexene, 3-methyl-1-pentene, 3,3-dimethyl-1-butene, 1,3-butadiene, and styrene.
ISSN:0022-328X
1872-8561
DOI:10.1016/0022-328X(87)85028-3