Table 3 Oxidation of various diols with TBHP catalyzed by THA
combined with FeCl3
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a
Entry
1b
Substrate
Product
Time/h
16
Conv. (%)
76
4 For Ru catalyzed oxidation: J.-E. Backvall, R. L. Chowdhury and
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U. Karlsson, J. Chem. Soc., Chem. Commun., 1991, 473;
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2b
3a
16
6
80
96
71
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4a
6
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a
Reaction conditions: 2.4 mmol of alcohol, 2.0 mol% of catalyst,
b
2.5 eq. TBHP, 80 1C for specific time. 3 mol% catalysts. The selectivity
and the conversion were determined via GC-MS.
J.-E. Backvall, Angew. Chem., Int. Ed., 2008, 47, 3506. For
¨
TEMPO associated oxidation: I. A. Ansari and R. Gree, Org.
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17 A. A. Linde
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18 See ESIw for experimental details and the optimized procedures
such as time effect, catalyst amount, oxidant amount and different
oxidant effect.
19 The in situ catalyst has been studied via ESI-MS. When in situ
catalyst in reaction mixture is dissolved in MeOH, the electrospray
ionization-mass spectrometry (ESI-MS) measurements show the
dominating peak patterns of moderate peaks at m/z = 419.9525
and 343.88. According to the isotope distribution they can be
assigned as [C14H14N4O8FeCl2] and [C7H7N2O4FeCl3] cations,
respectively. The software used for the simulations is Bruker
Daltonics Data Analysis (version 3.3) (see ESIw).
c
9252 Chem. Commun., 2010, 46, 9250–9252
This journal is The Royal Society of Chemistry 2010