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Phenanthrene-Based Triptycenes: Synthesis and Cascade Skeletal Transformations
Alexey S Zaikin1, Oleg A Levitskiy1, Dmitry A Dulov1
1Lomonosov Moscow State University , Moscow119991, Russia.
Abstract:
Novel members of the phenanthrene-based triptycene family are reported. A comparative DFT study of various approaches to the triptycene framework allowed adjustment of the reaction conditions for cycloaddition to anthracene not only for highly reactive arynes but also for normal alkynes, which has not yet been reported. Novel dibenzotriptycenes are prone to cascade skeletal transformations under both oxidative (PIFA) and electrophilic (Br2) conditions, yielding synthetically challenging indenophenanthrenes.
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