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Poly[manganese(II)(l-D-tartrate)] (3)
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Oxidation of cyclooctene, general procedure
Oxidation reactions were performed in a stirred round-
bottomed flask fitted with a water-cooled condenser.
Reactions were carried out under atmospheric pressure in
air in an oil bath at 60 1 °C with acetonitrile as co-
solvent and aqueous H2O2 (35%) as oxidant. Typically,
0.004 mmol of catalyst, 0.098 mmol of imidazole,
1.0 mmol of olefin, and 3 cm3 acetonitrile were added to
the flask. After the mixture had been heated to 60 1 °C,
an aqueous solution (1.0 cm3, 11.0 mmol) of H2O2 was
added. After the required time, the products were analyzed
by gas chromatography, gas chromatography–mass spec-
trometry, and 1H NMR spectrometry. To ensure
reproducibility, the oxidation experiments with H2O2 in the
different solvents with 1-bulk at 60 °C and a reaction time
of 24 h (cf. Fig. 5) were each repeated ten times (conver-
sions for single experiments varied within 2%). The
conversion percentage given in Fig. 5 is an average value
from these ten experiments. Excess H2O2 was slowly
decomposed to H2O and O2 during the oxidation reaction.
In the oxidation of cis and trans-stilbenes, the reaction
`
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´
1
1
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NMR spectra of the crude products were acquired. For cis-
stilbene, no traces of trans-stilbene were observed. These
findings confirmed that cis-stilbene is stable in the oxida-
tion reaction medium and does not isomerize to trans-
stilbene.
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Acknowledgments We are grateful to the Zanjan and Tarbiat
Modares Universities for financial support of this study, and for DFG
grant Ja466/14-1/2.
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