om500513m_si_002.cif (326.87 kB)
Synthesis and Coordination Chemistry of Pentadienyl Ligands Derived from (1R)‑(−)-Myrtenal
dataset
posted on 2015-12-17, 03:27 authored by Ann Christin Fecker, Bogdan-Florin Crăciun, Matthias Freytag, Peter
G. Jones, Marc D. WalterWith the natural product (1R)-(−)-myrtenal
as the starting material, a series of chiral pentadienes (Pdl*) such
as dimethylnopadiene (2a), methylphenylnopadiene (2b), and methylnopadiene (2c) have been prepared
by Wittig reactions. Deprotonation with the Schlosser base gives the
corresponding potassium pentadienides 3a-K–3c-K, whose structures were investigated by NMR spectroscopy
and X-ray diffraction studies. In all cases a “U” conformation
was observed. Furthermore, the coordination chemistry and electronic
properties of these new pentadienyl systems were explored in several
half-open trozircene complexes [(η7-C7H7)Zr(η5-Pdl*)] and their PMe3 and tBuNC adducts. Density functional theory (DFT)
computations are consistent with the experimentally observed face
selectivity upon metal coordination: namely, that the metal coordinates
exclusively from the sterically less encumbered side.
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DensitycomputationPentadienyl Ligands Derivedchiral pentadienesmethylnopadieneSynthesitBuNC adductsSchlosser basecoordination chemistryPMe 3seriesmetal coordinatestrozirceneDeprotonationpentadienidemetal coordinationconformationPdlmethylphenylnopadienepentadienyl systemsWittig reactionsCoordination ChemistrystericallyDFTpotassiumface selectivitydimethylnopadiene7HcomplexNMR spectroscopymaterialdiffraction
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