Intramolecular versus intermolecular mechanism of metallotropic rearrangements of chiral chromium tricarbonyl complexes of substituted naphthalenes and other polyaromatic compounds investigated by chiral HPLC of its racemic mixtures

Add time:08/02/2019    Source:sciencedirect.com

Pure enantiomers of chromium tricarbonyl complexes of α- and β-monosubstuted naphthalenes RC10H7Cr(CO)3 (R=Cl, Me, SiMe3, SnMe3) were separated as pure enantiomers by chiral phase HPLC on a Chiracel OD column. Inter-ring haptotropic rearrangements (IRHRs) (process in which metal shifts between substituted and non-substituted rings) of pure enantiomers were investigated in different solvents in the presence or absence of some solvating additives. It was shown that IRHR proceeds at 85°C in noncoordinative and noncomplexing solvents such as hexafluorobenzene or decane through an intermolecular mechanism without racemization. In aromatic toluene, which can bind with the organometallic group, it proceeds through a partially intramolecular mechanism, leading to considerable racemization (ca. 20%) of the complexes. In the presence of solvating additives (THF, dibutyl ether), almost complete racemization (>90%) was observed.

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