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

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

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Wiley-VCH Verlag GMBH

Abstract

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.

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Chemistry, A European Journal

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2037-12-31