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

Heinrich, Nora; Willis, Anthony; Cade, Ian; Ho, Junming; Coote, Michelle; Banwell, Martin

Description

Opening 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.

CollectionsANU Research Publications
Date published: 2012
Type: Journal article
URI: http://hdl.handle.net/1885/68360
Source: Chemistry, A European Journal
DOI: 10.1002/chem.201202903

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