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Type: Journal article
Title: Preparation and some chemistry of ferrocenylethynyl ketones
Author: Bruce, M.
Jevric, M.
Skelton, B.
Citation: Journal of Organometallic Chemistry, 2010; 695(3):453-462
Publisher: Elsevier Science Sa
Issue Date: 2010
ISSN: 0022-328X
Statement of
Michael I. Bruce, Martyn Jevric and Brian W. Skelton
Abstract: Reactions of Fc′(CHO)2 1 (Fc′ = 1,1′-ferrocenediyl) with LiC{triple bond, long}CR gave substituted propargylic alcohols Fc′{CH(OH)C{triple bond, long}CR}2 (R = SiMe3 2, Fc 9). Oxidation (MnO2) of these alcohols afforded the bis(alkynyl ketone)s Fc′{C(O)C{triple bond, long}CR}2 (R = SiMe3 3, Fc 10), the former being accompanied by the partially desilylated Fc′{C(O)C{triple bond, long}CH}-1-{C(O)C{triple bond, long}CSiMe3}-1′ 4. The reaction between 4 and RuCl(dppe)Cp in the presence of Na[BPh4] gave the cyclic vinylidene complex [Ru{{double bond, long}C{double bond, long}C[C(O)Fc′C(O)CH{double bond, long}CH]}(dppe)Cp]BPh4 5. The diastereomers were separated by flash chromatography (2) or preparative t.l.c. (9) to give the cis (2a, 9a) and trans (2b, 9b) isomers. Cyclisation of each isomer to the corresponding ferrocenophane was catalysed by pTSA to give Fc′{[CH(C{triple bond, long}CR)]2O} (R = SiMe3 6a, 6b; Fc 11a, 11b), of which 6a, 6b could be desilylated to Fc′{[CH(C{triple bond, long}CH)]2O} 7a, 7b, and further transformed into the bis(η2-alkyne-dicobalt) complexes Fc′{[CH(η2-C2H[Co2(μ-dppm)(CO)4])]2O} 8a, 8b with Co2(μ-dppm)(CO)6. Molecular structures of 3, 5, 6a, 6b, 7a, 7b and 10 were determined by single-crystal XRD methods. © 2009.
Keywords: Ferrocene
Rights: Copyright 2009 Published by Elsevier B.V.
DOI: 10.1016/j.jorganchem.2009.10.024
Grant ID: ARC
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