Reversible Cyclopropane Ring‐Cleavage Reactions within Etheno‐Bridged [4.3.1]Propelladiene Frameworks Leading to Aza‐ and Oxa‐[5.6.5.6]fenestratetraenes | Zendy

Heinrich Nora | Zendy; Willis Anthony C. | Zendy; Cade Ian A. | Zendy; Ho Junming | Zendy; Coote Michelle L. | Zendy; Banwell Martin G. | Zendy

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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.

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