The chemical behavior of ferrocenylboranes FcB(R)R‘ (Fc = C5H5FeC5H4) toward 2,5-bis(pyrazol-1-yl)benzoquinone (1) is highly dependent on the nature of the substituents R and R‘. Reaction of 1 with 2 equiv of the ferrocenylborane FcBMe2 (2a) results in an unprecedented sequence of methyl migration and elimination steps; the Fe(II) oxidation state of the Fc fragments remains unchanged. In contrast, electron-transfer processes involving iron oxidation and benzoquinone reduction dominate the reaction of 1 with FcB(Me)Br (2b) and FcBBr2 (2c). Despite these different reactivities, bis(ferrocenyl) complexes with a bridging hydroquinone ligand (3a, [3b]Br2, [3c]Br2) are formed in all three cases.

Ding, L., FABRIZI DE BIANI, F., Bolte, M., Zanello, P., & Wagner, M. (2000). Reactivity of ferrocenylboranes: rearrangements versus electron transfer reactions. ORGANOMETALLICS, 19, 5763-5768 [10.1021/om000727w].

Reactivity of ferrocenylboranes: rearrangements versus electron transfer reactions

FABRIZI DE BIANI, FABRIZIA;ZANELLO, PIERO;
2000

Abstract

The chemical behavior of ferrocenylboranes FcB(R)R‘ (Fc = C5H5FeC5H4) toward 2,5-bis(pyrazol-1-yl)benzoquinone (1) is highly dependent on the nature of the substituents R and R‘. Reaction of 1 with 2 equiv of the ferrocenylborane FcBMe2 (2a) results in an unprecedented sequence of methyl migration and elimination steps; the Fe(II) oxidation state of the Fc fragments remains unchanged. In contrast, electron-transfer processes involving iron oxidation and benzoquinone reduction dominate the reaction of 1 with FcB(Me)Br (2b) and FcBBr2 (2c). Despite these different reactivities, bis(ferrocenyl) complexes with a bridging hydroquinone ligand (3a, [3b]Br2, [3c]Br2) are formed in all three cases.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11365/20025
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