Ironsilicon bond cleavage in dicarbonyl(ν 5-cyclopentadienyl)(trimethylsilyl)iron using tetrabutylammonium fluoride

• Published in: Journal of organometallic chemistry Vol. 251; no. 1; pp. 71 - 78
• Main Authors: Marten, David F., Wilburn, Susan M.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.01.1983
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/0022-328X(83)80245-9

Dicarbonyl(η 5-cyclopentadienyl)(trimethylsilyl)iron ( 1) was found to react with a 1 M solution of tetrabutylammonium fluoride ( 2) in tetrahydrofuran at 25°C to give dicarbonyl(η 5-cyclopentadienyl)iron anion ( 5). The anion generated under these conditions was trapped with electrophiles (RX) to give 45–89% yields of neutral dicarbonyl(η 5-cyclopentadienyl)-alkyl, -allyl, -acyl-iron compounds and the ethylene cation. Tetrabutylammonium hydroxide also can be used in this reaction. Evidence indicates that fluoride ion instead of hydroxide attacks the silicon when tetrabutylammonium fluoride is used since fluorotrimethylsilane can be detected in the reaction product. Tetrabutylammonium fluoride and hydroxide quantitatively liberate styrene from dicarbonyl(η 5-cyclopentadienyl)(η 2-styrene)iron tetrafluoroborate, producing bis[dicarbonyl(η 2-cyclopentadienyl)iron].