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All NMR spectra were recorded on a Bruker Avance 400
spectrometer. Deuterated NMR solvents were obtained from
Cambridge Isotope Laboratories, Inc., Andover MA, and
used without further purification. All products were confirmed
by comparison to literature 1H NMR (di-(4-bromobenzyl)
carbonate,18 dibenzyl carbonate,54 di-phenethylcarbonate,44 di-
dodecyl carbonate,55 di-pentyl carbonate,44 di-(4-bromobenzyl)
urea56). 4-bromobenzyl bromide, 18-crown-6, benzyl chloride,
benzyl bromide, 1-bromododecane, 1-bromopentane and (2-
bromoethyl)benzene were purchased from Acros Organics and
used without further purification. Sodium hydroxide and potas-
sium carbonate were purchased from Fisher Chemical and
used without further purification. Ball milling was carried out
in an 8000 M SpexCertiprep Mixer/Mill. Ball bearings were
purchased from Small Parts incorporated. Custom made vials
were made by the machine shop at the University of Cincinnati
with metal rods purchased from ESPICorp Inc.
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Dialkyl carbonate
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Potassium carbonate (0.69 g, 0.5 mmol), 18-crown-6 (0.264 g,
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1
vial along with a 3/16¢¢ inch stainless steel ball bearing. The
vial was placed in an 8000 M Spex Certiprep mixer/mill and
the contents were ball milled for 2 h. The resulting mixture was
dissolved in ethyl acetate (15 mL) and washed with H2O (3 ¥
15 mL). The organic layer was dried over anhydrous MgSO4
and the solvent was evaporated under reduced pressure. This
afforded di-(4-bromobenzyl) carbonate in a 74% conversion.
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Acknowledgements
We would like to thank the National Science Foundation (CHE-
0548150) and the University of Cincinnati’s Research Council
(URC) for the financial support for this research. We would
also like to thank the National Science foundation-iREU, The
American Chemical Society and the Deutscher Akademischer
Austausch Dienst for the financial support for Indre Thiel to
conduct the research.
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