Inorganic Chemistry
Communication
Notably, the only oxidized organic products with the 1%
catalyst loading are epoxides. This again contrasts with other
reported group 13 catalyzed alkene epoxidations, which
produce sizable amounts of alcohols and ketones/alde-
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
1
2−15
hydes.
This selectivity is lost as the catalyst loading is
We thank Auburn University and the American Chemical
Society, donors of the Petroleum Research Fund (Grant 49532-
DNI3), for financial support and Prof. John Odom for his
assistance in acquiring the ICP-OES data.
lowered. With a gallium(III) loading of 0.1%, the major
products are 3-cyclohexenol (39%) and 1,2-cyclohexanediol
(
51%); the yield of cyclohexene oxide is only 8%. The new
products do not result from further chemical transformation of
the epoxide; epoxides do not react with the Ga /PAA mixtures
III
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ASSOCIATED CONTENT
Supporting Information
X-ray crystallographic data in CIF format, experimental section,
isolated yields, full crystallographic data for [Ga(phen) Cl ]Cl,
ICP-OES data, control studies, yield of cyclooctene epoxidation
as a function of time, MS analysis of cyclooctene epoxidation at
s and 60 min, and a summary of alkene epoxidation catalyzed
■
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*
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(
AUTHOR INFORMATION
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dx.doi.org/10.1021/ic300159a | Inorg. Chem. 2012, 51, 2725−2727