4454
P. Tang, T. Ritter / Tetrahedron 67 (2011) 4449e4454
Furuya, T.; Strom, A. E.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 1662e1663; (g) Ball,
1.10 equiv),
and
1-chloromethyl-4-fluoro-1,4-diazoniabicyclo
N. D.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 3796e3797; (h) Wang, X.; Mei,
T.-S.; Yu, J. Q. J. Am. Chem. Soc. 2009, 131, 7520e7521; (i) Furuya, T.; Benitez, D.;
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[2.2.2]-octane bis(trifluoroborate) (1) (3.54 g, 10.0 mmol,
2.00 equiv). The reaction mixture was stirred at 90 ꢀC for 2 h in
a 350 mL sealed vessel. The reaction mixture was cooled to 23 ꢀC
and concentrated under reduced pressure. The residue was washed
with CH2Cl2 (3ꢃ20 mL) and the solid was dissolved in 250 mL
HNO3 (10%, v/v in H2O). After stirring for 30 min at 23 ꢀC, the re-
action mixture was filtered. To the filtrate was added NaOH (10%, v/
v in H2O, 250 mL). The suspension was filtered and the solid residue
washed with water (3ꢃ20 mL) to afford 1.86 g Ag2O (80%) as
a brown powder.
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We thank the NSF (CHE-0952753) and the NIH-NIGMS
(GM088237) for financial support. We thank Air Products and
Chemicals, Inc. for a generous donation of F-TEDA-BF4.
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Supplementary data
Supplementary data includes detailed experimental procedures
and spectroscopic data for all new compounds. Supplementary data
associated with this article can be found online at doi:10.1016/
most important compounds described in this article.
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