Ring-opening addition of hydrogen chloride to monocyclic and spirocyclic [1]ferrocenophanes: a convenient and controlled route to ferrocenylchlorosilanes and germanes

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Abstract
The ring-opening addition of HCl to [1]ferrocenophanes has been shown to provide a general method for the preparation of chlorosilanes and germanes with ferrocenyl substituents. Reaction of HCl with dimethyl[1]silaferrocenophane, fcSiMe2 (1a) [fc=Fe(η-C5H4)2], affords chlorodimethylferrocenylsilane, FcMe2SiCl (3a) [Fc=(η-C5H4)Fe(η-C5H5)], in 68% yield. Trichloroferrocenylsilane, FcSiCl3 (3b), and chlorodimethylferrocenylgermane, FcMe2GeCl (3c), were prepared by an analogous route from ferrocenophanes fcSiCl2 (1b) and fcGeMe2 (1c). Ring-opening addition of HCl to the spirocyclic [1]ferrocenophane, fcSi(CH2)3 (4), leads to cleavage of the Si–C bond of the strained ferrocenophane, giving the silacyclobutane FcSiCl(CH2)3 (5) in 84% yield. Moreover, treatment of the spirocyclic [1]silaferrocenophane fc2Si (6) with HCl affords orange crystals of dichlorodiferrocenylsilane, Fc2SiCl2 (7), in 88% yield. Hydrolysis of 7 in the presence of triethylamine generated diferrocenylsilanediol, Fc2Si(OH)2 (8), in 90% yield. A single crystal X-ray diffraction study combined with spectroscopic identification confirmed that 8 crystallizes in a new bead-and-chain motif.

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