A solvent-controlled regioselective rearrangement reaction of spiroindane-1,3-diones with a leaving group has been developed. In acetonitrile solvent, the spiroindane-1,3-diones were rearranged to provide tritylone alcohols, while 2-benzoylbenzoate ester derivatives were obtained if the reactions were performed in alcohols.
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Switchable Synthesis of Tritylone Alcohols and 2-Benzoylbenzoate Esters from Spiroindane-1,3-diones.
J Org Chem
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Department of Chemistry, National Chung Hsing University, Taichung City, Taiwan 40227, Republic of China.
A solvent-controlled regioselective rearrangement reaction of spiroindane-1,3-diones with a leaving group has been developed. In acetonitrile solvent, the spiroindane-1,3-diones were rearranged to provide tritylone alcohols, while 2-benzoylbenzoate ester derivatives were obtained if the reactions were performed in alcohols.
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Photochem Photobiol Sci
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Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.
The 9-phenyl-9-tritylone photoremovable protecting group was examined using both photoproduct analysis and laser flash photolysis in order to determine the details of its mechanism of alcohol release. It is shown that formation of the tritylone anion radical is required for alcohol release. Attempts to trigger release via intramolecular photoinduced electron transfer were unsuccessful due to rapid back electron transfer reactions of the triplet diradical anion.
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Department of Chemistry and Biochemistry, University of Maryland , College Park, Maryland 20742, United States.
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