Reversible Cyclopropane Ring-Cleavage Reactions within etheno-bridged [4.3.1]propelladiene frameworks leading to aza- and oxa-[5.6.5.6] fenestratetraenes

Heinrich, NoraWillis, AnthonyCade, IanHo, JunmingCoote, MichelleBanwell, Martin2015-12-100947-6539http://hdl.handle.net/1885/68360Opening and closing a chemical window: Oxidation of the etheno-bridged [4.3.1]propelladienol 1 with pyridinium chlorochromate (PCC) affords oxa[5.6.5.6]fenestratetraene 2. The reduction of 2 with diisobutylaluminum hydride (DIBAl-H) leads to the regeneration of its precursor (1; see scheme). These transformations most likely involve a [3,5]-sigmatropic rearrangement process.Keywords: Chemical window; Cleavage reaction; Diisobutylaluminum hydride; fenestratetraenes; norcaradienes; Pyridinium chlorochromate; Ring-cleavage reaction; Sigmatropic rearrangements; Chemistry; Synthesis (chemical); Propane; aza(5.6.5.6)fenestratetrene; bridged cleavage reactions; fenestratetraenes; norcaradienes; salvileucalin B; sigmatropic rearrangementReversible Cyclopropane Ring-Cleavage Reactions within etheno-bridged [4.3.1]propelladiene frameworks leading to aza- and oxa-[5.6.5.6] fenestratetraenes201210.1002/chem.2012029032016-02-24