1542
L. Sbaragli, W.-D. Woggon
PAPER
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Finnigan GC-FID/SUPELCOWAX 10/gradient 100–260 °C).
Compounds were identified by distinct retention times: 3.9 min
(13), 10.3 min (16), 13.0 min (18), 14.9 min (17); and by co-injec-
tion with authentic material; >99% GC-pure 13, 16, 17 and 18 were
prepared according to slightly modified published procedures.27
The following product ratio was obtained: 17/(16 + 18) = 2:1 and
18/16 = 9:1. Oxidation experiments were repeated four times and
standard deviation of 5% was determined for product ratios. Fur-
ther, control experiments showed that 18 does not rearrange to 16 in
the presence of PhIO.27
Acknowledgment
(16) Newcomb, M.; Toy, P. H. Acc. Chem. Res. 2000, 33, 449.
(17) Kozuch, S.; Leifels, T.; Meyer, D.; Sbaragli, L.; Shaik, S.;
Woggon, W.-D. Synlett 2005, 765.
(18) Poulos, T. L. J. Biol. Inorg. Chem. 1996, 1, 356.
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S.; Ogliaro, F.; Shaik, S. J. Am. Chem. Soc. 2002, 124, 8142.
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1989, 72, 391.
We thank Martin Newcomb for a sample of 13 for preliminary ex-
periments. Financial support from the Swiss National Science
Foundation is gratefully acknowledged.
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Synthesis 2005, No. 9, 1538–1542 © Thieme Stuttgart · New York