Jeong-Ae Ahn et al.
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Table 3. Rh(I)-catalyzed C C bond activation ofvarious ketones with
several alkenes.
References and Notes
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[a]
GC yield based on 1 and values in parenthesis are isolated yields.
The ratio was determined by H NMR.
[b]
[c]
1
7 equivs. ofoleifn were used under 100 mol %
10 mol% benzoic acid.
4, 15 mol % 5, and
crowavereactor. Thereactionwascarriedoutwithinternalmag-
netic stirring for 5 min to ensure homogeneous conditions at
2008C under microwave irradiation. After cooling, the reaction
mixture was filteredthrough a short column filled withsilicaand
washed with CH2Cl2 and ethyl acetate. The filtrate was analyzed
by GC and GCD, and determined as 44% of2-acetylnorbonane
(6a, exo- and endo-mixtures) and 40% ofstyrene ( 7a). A ratio of
exo- and endo-2-acetylnorbonanes was determined by 1H NMR
spectroscopy. 2-Acetylnorbonane comprised an exo and endo-
mixtures in a ca. 72/28 ratio. When the reaction was carried
out with additional cyclohexylamine (5a, 20 mol % based on
1a), 85% of 6a and 84% of 7a were determined.
Ed. 2004, 43, 6250.
[7] The MW reaction was performed using a CEM Discover
monomode reactor with measurement and monitoring of
temperature by IR detection and power modulation be-
tween 15–300 W.
[8] Since 2-acetylnorbonane (6a) is volatile, isolated yields
were not accurate, and yields were determined by GC.
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Acknowledgements
This work was supported by grant No. R01-2005-000-10548-0
from the Basic Research Program of the Korea Science & Engi-
neering Foundation.
58
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Adv. Synth. Catal. 2006, 348, 55 – 58