Semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and -2-ol |
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| Authors: | Xiaofang Wang Yuxiang Dong Edward L Ezell Jered C Garrison James K Wood James P Hagen Jonathan L Vennerstrom |
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| Institution: | 1. College of Pharmacy, University of Nebraska Medical Center, Omaha, NE, 68198, United States;2. Eppley Institute for Research in Cancer, University of Nebraska Medical Center, Omaha, NE, 68198, United States;3. Department of Chemistry, University of Nebraska-Omaha, Omaha, NE, 68182, United States |
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| Abstract: | A number of new polybrominated adamantanes were formed by rearrangements and bromination of 2,2,6,6-tetrabromoadamantane under Friedel-Crafts conditions. Protoadamantane-4,10-dione, 10-acetoxyprotoadamantan-4-one, 1,2,6-triacetoxyadamantane and 5,6-diacetoxyadamantan-2-one were formed by successive semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and 5,6-dibromoadamantan-2-ol. This work may open up new pathways for the synthesis of 1,2,6-trisubstituted adamantanes. |
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| Keywords: | Semipinacol rearrangement Protoadamantane-adamantane rearrangement Polybrominated adamantanes 1 2 6-Trisubstituted adamantanes |
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