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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
Author(s) -
Heinrich Nora,
Willis Anthony C.,
Cade Ian A.,
Ho Junming,
Coote Michelle L.,
Banwell Martin G.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201202903
Subject(s) - cyclopropane , chemistry , sigmatropic reaction , pyridinium , cleavage (geology) , pyridinium chlorochromate , ring (chemistry) , stereochemistry , hydride , medicinal chemistry , hydrogen , organic chemistry , materials science , fracture (geology) , composite material
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.