Organometallics
Article
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(28) The isomeric bimetallic systems represented by variants I and
III−V possess a plane of symmetry splitting the structures into equal
monometallic fragments. Thus, the first initiation step of the bimetallic
complexes can release only one type of monometallic complex,
irrespective of which metal center is released first. In turn, the
bimetallic complex related to variant II has two different metallic
centers, and two different monometallic species are thus possible. This
makes its activity behavior complicated and stopped us from further
consideration of the system.
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(12) Apart from the steric and electronic effects we considered a
CH−π interaction of the RuCH group with the aromatic arm of
NHC ligand, HOMO/LUMO levels of the naphthalene ligand, and
the coordinating abilities of oxygen atoms derived from 1- and 2-
naphthol. However, energetic factors corresponding to the observed
differences of the (pre)catalysts’ initiation rates must come from
sources other than those initially considered.
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(29) In complexes 33, 34, and 37−39 we reduced the coordinating
iPrO groups into the MeO groups to minimize the number of possible
conformations. For studies of the related monometallic MeO-
coordinated systems, see ref 11a and: (a) Barbasiewicz, M.; Bieniek,
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(15) The rate-determining step of the (pre)catalysts’ initiation is
chelate opening, and once the chelate opens (entirely or partially in
the transition state),10,11 the cyclic π-electron delocalization within the
chelate must be suppressed.13 Thus, under the conditions of our
activity studies we attribute the low activity of the complexes (kinetics)
to aromatic stabilization of the chelate rings (thermodynamics).
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(30) Literature procedures for the ligand exchange reactions apply to
substrates bearing both vinyl and propenyl substituents. In some cases
propenyl derivatives give better results than vinyl species and are less
prone toward ligand dimerization under the ligand exchange
conditions. See: Bieniek, M.; Michrowska, A.; Gułajski, Ł.; Grela, K.
Organometallics 2007, 26, 1096−1099. In the synthesis of the
monometallic complexes we successfully used propenyl derivatives as
E/Z mixtures of isomers. However, when selectivity issues in the
synthesis of the bimetallic species were first encountered, we changed
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dx.doi.org/10.1021/om3001372 | Organometallics 2012, 31, 3636−3646