期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2020, 期 42, 页码 6576-6587出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202001032
关键词
Chloroferrocenes; Ferrocenyl thioethers; Halogen dance; Cyclopentadienyl ring exchange; Crystal structure
资金
- Deutsche Forschungsgemeinschaft
The pentachloroferrocenes [C5Cl5]Fe[C5H4X] (X = H, Br, SMe) react with LiTMP and MeSSMe to form mixtures of compounds, that contain besides the expected products of deprotonation also one or more complexes with a [C5Cl4(SMe)] ligand. This latter observation makes the otherwise rarely observed occurrence of halogen dance reactions in chloroaromatics very probable. 1,2,3-Trichloroferrocene yields with BuLi and MeSSMe products of both halogen-metal-exchange and of deprotonation. Additionally, in all examined systems, the observation of some highly-substituted complexes with eight or more substituents hints to the involvement of cyclopentadienyl exchange reactions, which has also rarely been observed under such mild conditions. The molecular structures of [C5Cl4(SMe)]Fe[C5H3BrX] (X = SMe or SOMe), [C5Cl4(SMe)]Fe[C5H2Cl(SMe)(2)], [C5Cl2(SMe)(3)](2)Fe, and [C5HCl3(SMe)](2)Fe have been determined by X-ray diffraction.
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