“…Acetyl Ferrocene 1 13 The spectra were in agreement with the structure in [16,38,39]. For this new compound, we made tentative assignments based on the spectra of related structures such as vinyl ferrocene [36] and some ferrocenyl chalcones [37].…”
Section: -Spectroscopic Characteristics Of the Ferrocene Derivativessupporting
“…Acetyl Ferrocene 1 13 The spectra were in agreement with the structure in [16,38,39]. For this new compound, we made tentative assignments based on the spectra of related structures such as vinyl ferrocene [36] and some ferrocenyl chalcones [37].…”
Section: -Spectroscopic Characteristics Of the Ferrocene Derivativessupporting
“…Thus a dynamic process involving the rotation of the aromatic ketone around the C 6 -C 13 vector which discriminates H 7 /H 10 and H 8 /H 9 is proposed (see Scheme 1 for atom numbering). The potential barrier for the sterically less encumbered benzoyl ferrocene has been determined as 28 kJ mol À1 [20]. Unfortunately, amine 3 shows only general broadening of all signals due to beginning precipitation at lower temperatures preventing any barrier estimation.…”
“…While I will be favored by hard acid counterions such as Li + , π-bound counterions such as Fe II will favor II . Consistent with this picture, the ring−CHO rotational barrier for KC 5 H 5 CHO (61 kJ mol -1 ) exceeds that of formylferrocene (37 kJ mol -1 ) 4 Molecular orbital diagram for (C 5 H 5 )Fe(C 5 H 4 C(O)NH 2 ).…”
Section: Resultsmentioning
confidence: 54%
“…On the basis of the limiting low-temperature chemical shift differences (ca. 50−100 Hz) observed for the H 2 resonance in compounds with larger barriers (for example, 37 kJ mol -1 in formylferrocene), coalescence temperatures for ring−CONR 2 rotation of ca. −150 °C might be anticipated for amidoferrocenes.…”
A molecular mechanics force field has been developed for the conformational analysis of
amido- and α-aminoferrocenes. Parameterization for ring-substituent rotational barriers in
amidoferrocenes and other cross-conjugated derivatives have been calculated using DFT on
both the free and complexed cyclopentadienyl ligand. Modeled structures of (diisopropylamido)- and (dimethylamido)ferrocene and N,N-dimethyl-α-ferrocenylethylamine are in
agreement with those determined through single-crystal X-ray diffraction. The diastereoselective lithiation of N,N-dimethylferrocenylethylamine and sparteine-mediated enantioselective lithiation of (diisopropylamido)ferrocene using MeLi have been modeled through
an assumed reversible adduct formation at the amine nitrogen or amide oxygen, followed
by an irreversible ring lithiation. Results indicate that selectivity results from ring lithiation
via the adduct conformer with the shortest C−Hring- - -H3C−Li interaction.
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