Hydroquinoid Chromium Complexes Bearing an Acyclic Conjugated Bridge: 
Chromium-Templated Synthesis, Molecular Structure, and Haptotropic Metal 
Migration

Hegele, Peter; Santhamma, Bindu; Schnakenburg, Gregor; Fröhlich, Roland; Kataeva, Olga; Nieger, Martin; Kotsis, Konstantinos; Neese, Frank; Dötz, Karl Heinz

doi:10.1021/om100257x

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Hydroquinoid Chromium Complexes Bearing an Acyclic Conjugated Bridge: Chromium-Templated Synthesis, Molecular Structure, and Haptotropic Metal Migration

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Hegele, P., Santhamma, B., Schnakenburg, G., Fröhlich, R., Kataeva, O., Nieger, M., et al. (2010). Hydroquinoid Chromium Complexes Bearing an Acyclic Conjugated Bridge: Chromium-Templated Synthesis, Molecular Structure, and Haptotropic Metal Migration. Organometallics, 29(23), 6172-6185. doi:10.1021/om100257x.

Cite as: https://hdl.handle.net/21.11116/0000-0008-0F7E-C

Abstract

The naphthohydroquinoid tricarbonyl chromium complexes 3 and 6, bearing a styryl or phenylazo moiety, have been synthesized and studied for the haptotropic metal migration along the extended π-system. Quantum chemical calculations suggested a feasible stepwise rearrangement of the Cr(CO)₃ fragment from the hydroquinoid to the other terminal phenyl ring for the azo- rather than for the ethene-bridged system. An experimental and kinetic study of the ethene-bridged complex 3 revealed a haptotropic metal shift onto the adjacent naphthalene ring to give isomer 7 and suggested a competing intermolecular decomplexation−recomplexation pathway for the coordination of the terminal phenyl ring, affording bismetalated complexes 8 and 9. Attempts of a controlled metal migration in the azo complex analogue 6 under similar conditions were unsuccessful and resulted in partial decomposition.