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Protonation and rearrangement of the tricyclo[4.2.2.2]dodeca-3,7,9,11-tetraene scaffold |
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| Authors: | Derong Cao Sheyang Xu Chunmei Gao Herbert Meier |
| Institution: | a College of Chemistry, South China University of Technology, 510640 Guangzhou, China b LCLC, Guangzhou Institute of Chemistry, Chinese Academy of Sciences, 510650 Guangzhou, China c Graduate School of CAS, Beijing 100039, China d Institute of Organic Chemistry, University of Mainz, D-55099 Mainz, Germany |
| Abstract: | The biplanemers 2a,b contain enol ether substructures, which permit facile protonations of the π electron system. The subsequent ether cleavage is characterized by rearrangements of the polycyclic scaffold of the carbenium ions or the electroneutral primary products. Apart from the expected products 3a and 5a, a series of unexpected ketones and diketones (4a′, 9b, 10b, 11b, and 12b) were obtained. |
| Keywords: | Carbenium ions Hydrolysis Rearrangements Cyclic ketones |
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