Gleixner, Renate M., Joly, Kévin M., Tremayne, MaryJane, Kariuki, Benson  ORCID: https://orcid.org/0000-0002-8658-3897, Male, Louise, Coe, Diane M. and Cox, Liam R.
2010.
Reaction of 1,1'-Divinyl ferrocene with one-electron oxidants: entry into functionalised [4]ferrocenophanes and observation of an isotope-dependent chemoselectivity effect.
Chemistry: A European Journal
16
(19)
, pp. 5769-5777.
10.1002/chem.200903478
|
Abstract
1,1′-Divinyl ferrocene (2) reacts with K3[Fe(CN)6] under basic biphasic conditions to give a [4]ferrocenophane (4) in good yield. Incorporating deuterium labels into the internal positions of the vinyl groups of 2 affects the chemoselectivity of the reaction; thus under identical reaction conditions, [D2]-2 reacts to provide a diol-functionalised [4]ferrocenophane, [D2]-D/L-6 in addition to the expected keto-alcohol, [D1]-4. Variants on this one-electron oxidative cyclisation methodology can be used to give other [4]ferrocenophanes; thus, the reaction of 2 with CuCl2 in MeOH or iPrOH leads to dialkoxy [4]ferrocenophanes 19 and 20, respectively, whereas the reaction of 2 with benzyl carbamate in the presence of tBuOCl gives a bis(carbamate)[4]ferrocenophane, 21. Mechanisms to account for the formation of the products, the stereoselectivity, and the unusual isotope-dependent chemoselectivity in the reaction of 2 and [D2]-2 with K3[Fe(CN)6] are proposed.
| Item Type: | Article |
|---|---|
| Date Type: | Publication |
| Status: | Published |
| Schools: | Chemistry |
| Subjects: | Q Science > QD Chemistry |
| Uncontrolled Keywords: | cyclization; cyclophanes; isotope effects; metallocenes |
| Publisher: | Wiley |
| ISSN: | 0947-6539 |
| Last Modified: | 19 Oct 2022 09:51 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/22393 |
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