COMMUNICATIONS
mentioned are relative to this reference electrode which has
a voltage difference of +150 mV versus a standard hydro-
gen electrode (SHE). The working electrode was pretreated
by mechanical polishing. It was subjected to sequential pol-
ishing with a cloth covered with alumina powder of 1 and
0.05 mm particle size (SPI supplies, USA) for 10 min. To
remove any adherent Al2O3 particles, the electrode surface
was rinsed thoroughly with deionized water and cleaned in
an ultrasonic bath containing deionized water for 2 min.
Next, the electrode was rinsed with acetone and dried. Solu-
tions of 0.1M Bu4NBF4 in DMF were freshly made and
purged with nitrogen gas for 10 minutes to remove oxygen
before each measurement. Products are added through
a septum. For measurements at 808C the electrochemical
cell was placed in an oil bath.
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Electrolysis Experiments
A homemade airtight electrolysis cell was used equipped
with a reticulated vitreous carbon (RVC) as working elec-
trode (basi, USA), a bridged Ag/AgCl reference electrode
with 2M LiCl ethanol solution as inner solution and a 0.1M
Bu4NBF4/DMF as bridge solution was used and the counter
electrode, a platinum rod electrode, was put in a divided cell
separated from the anodic part by a ceramic frit. In a typical
electrolysis experiment 4 mL of a 0.2M Bu4NBF4 DMF solu-
tion were added to the divided part followed by the addition
of 200 mL of acetic acid. In the anodic part Shvo complex
(0.05 equivalent, 38 mg) and 2,6-dimethoxybenzoquinone
(0.25 equivalent, 29 mg) were added to a 0.2M solution of
Bu4NBF4 in DMF (14 mL). The cell was closed and placed
under an argon atmosphere. Stirring was started and the cell
was placed in an oil bath for heating, next a potential of
0.7 V was applied and finally the alcohol (0.7 mmol) was
added. After the appropriate reaction time the reaction mix-
ture was cooled down and water (30 mL) was added. The re-
sulting mixture was extracted with tert-butyl methyl ether (3
times 25 mL). The collected organic layer was washed with
0.2M HCl (15 mL) to further remove DMF. Next the organ-
ic layer was dried with MgSO4, filtered and evaporated. The
resulting solution was examined by NMR. Isolated products
were obtained using column chromatography on silica gel
with heptane/ethyl acetate (95/5) as eluent.
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Acknowledgements
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This work was financially supported by the University of
Antwerp (BOF), the Research Foundation – Flanders (FWO)
and the Hercules Foundation.
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