Interception and Synthetic Application of Diradical and Diene Forms of Dual‐Nature Azabicyclic o‐Quinodimethanes Generated by 6π‐Azaelectrocyclization
Majji Shankar,
Daniel J. Lee,
Supuni I. N. Hewa Inaththappulige
et al.
Abstract:We demonstrate that 2‐alkenylarylaldimines and ketimines undergo thermal 6p‐azaelectrocyclization to generate a wide range of azabicyclic o‐quinodimethanes (o‐QDMs). These o‐QDMs exist as a hybrid of a diene and a benzylic diradical. The diradical nature was confirmed by their ability to undergo dimerization and react with H‐atom donor, 2,2,6,6‐Tetramethylpiperidin‐1‐yl)oxyl (TEMPO) and O2. In addition, the interception of the diradicaloid o‐QDMs by H‐atom transfer was used to synthesize five tetrahydroisoquin… Show more
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