Jennifer L. Montgomery

Virginia Tech

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Frank R. Fronczek

Louisiana State University

Paul A. Deck

Virginia Tech

Michael J. Lane

Royal Brisbane and Women's Hospital

Carla Slebodnick

Virginia Tech

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Louisiana State University

Virginia Tech

University of Windsor

Baton Rouge Clinic

University of Kentucky

University of Louisiana at Lafayette

Bharathiar University

Illinois College

Bolu Abant İzzet Baysal University

Mississippi State University

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Synthesis and Structural Trends in Pentafluorophenyl-Substituted Ferrocenes, 1,4-Tetrafluorophenylene-Linked Diferrocenes, and 1,1‘-Ferrocenylene−1,4-Tetrafluorophenylene Co-oligomers

Organometallics (2000)

Paul A. Deck Michael J. Lane Jennifer L. Montgomery Carla Slebodnick Frank R. Fronczek

1,1'-Dilithioferrocene, or (CpLi)2Fe (1), reacts with excess C6F6 in THF to afford mostly (C6F5Cp)2Fe (2), accompanied by the diiron complex (C6F5Cp)FeCp(1,4-C6F4)CpFe(CpC6F5) (3). The reaction of 1 with 1.0 equiv of C6F6 affords a mixture of sparingly soluble step-growth oligomers assigned to [−FeCp(1,4-C6F4)−]n (4). [1-Li-2-RNCp]FeCp (6, RN = CH2NMe2) reacts with 1 equiv of C6F6 to afford [1-(C6F5)-2-RNCp]FeCp (7). Complex 6 reacts with 0.5 equiv of C6F6 to afford CpFe[2-RNCp](1,4-C6F4)[2-RNCp]FeCp as a mixture of two diastereomers (meso-8, major and dl-8, minor). The relative stereochemistry of meso-8 is established by crystallographic analysis of the corresponding bis(methiodide) (12). [1-Li-2-RNCp]Fe(CpLi) (9) reacts with excess C6F6 to afford mainly the diarylated ferrocene [1-(C6F5)-2-RNCp]Fe(CpC6F5) (10). The reaction of 9 instead with 1.0 equiv of C6F6 affords a mixture of oligomeric species assigned to the formula [−(2-RNCp)FeCp(1,4-C6F4)−]n (11). In contrast to 4, 11 is sufficiently soluble for characterization by solution NMR spectroscopy (end group analysis), and under optimized conditions a number-averaged degree of oligomerization corresponding to a linear Fe9 species is determined. The complexes 3, 7, 10, and 12 are characterized by single-crystal X-ray diffraction. Crystalline 3 exhibits infinite π-stacking interactions composed of intramolecular "triple-decker" C6F5−C6F4−C6F5 stacking and intermolecular Cp−C6F5 stacking. The crystal structure of 10 also shows intramolecular arene stacking, but intermolecular Cp−C6F5 interaction is interrupted by the dimethylaminomethyl substituent. None of these complexes show intermolecular stacking among the various C6F5 and C6F4 groups. Extensive intermolecular C−H···F−C interactions in the crystallographic packing diagrams of 3, 7, 10, 12, and CpFeCpC6F4C6F4CpFeCp (13) are characterized as either "purposeful" or "diffuse" by examining correlations of their respective H···F distances and C−H···F angles. Solution voltammetry of 3 shows two unresolved, reversible FeII|FeIII couples, suggesting weak electronic communication between the two iron centers despite the fully conjugated structure.

Diastereomer

10.1021/om990930v

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