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Lookup NU author(s): Lucinda Male, Professor William Clegg, Dr Luca Russo
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1,1'-Ferrocene biscarboxaldehyde (1) has been prepared and the aldehyde groups were subsequently protected with acetal groups to produce 1,1'-bisacetalferrocene (2). A ring-locked ferrocene was synthesised by further derivatisation of the cyclopentadiene rings at the 2,2' positions with phosphine substituents to produce 2,2'-bis-(acetal)-1,1'-diphenylphosphinoferrocene (3), which was subsequently coordinated to either a nickel chloride (5) or nickel bromide (6) metal centre. The ring-locked ferrocene complexes produced 2,5'-bis-(acetal)-1,1'-diphenylphosphinoferrocene substitution patterns. The acetal protecting groups of 2,2'-bis-(acetal)-1,1'-diphenylphosphinoferrocene were removed to produce 1,1'-bis-carboxaldehyde-2,2'-diphenylphosphinoferrocene (4). The Cp rings of 1,1'-bisacetalferrocene were also further derivatised at the 2,2' positions with a silane to produce the ring-locked 1,1'-siloxane-2,5'-bisacetalferrocenophane (7). The acetal protecting groups were removed from this to produce 1,1'-siloxane-2,5'- ferrocenophanecarboxaldehyde (8). For both the phosphine and siloxane electrophiles, the substitution on the Cp rings gives chiral products (obtained as racemic mixtures). Due to the highly regioselective nature of the reaction and diastereoselectivity in the products only C-2-symmetric compounds were observed without the presence of meso diastereoisomers. Subsequent ring-locking forced the Cp rings to rotate, leading to 1,1'-ring-locked ferrocenes with 2,5'-arrangement of the acetal groups (i.e. on opposite faces of the ferrocene unit). (c) 2009 Elsevier B.V. All rights reserved.
Author(s): Connell A, Holliman PJ, Butler IR, Male L, Coles SJ, Horton PN, Hursthouse MB, Clegg W, Russo L
Publication type: Article
Publication status: Published
Journal: Journal of Organometallic Chemistry
Year: 2009
Volume: 694
Issue: 13
Pages: 2020-2028
ISSN (print): 0022-328X
ISSN (electronic): 1872-8561
Publisher: Elsevier S.A.
URL: http://dx.doi.org/10.1016/j.jorganchem.2009.01.049
DOI: 10.1016/j.jorganchem.2009.01.049
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