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Divergent Synthesis of Helical Ketone Enabled by Rearrangement of Spiro Carbocation.

Limin WangLonghui DuanBiqiong HongZhenhua Gu
Published in: Organic letters (2023)
An acid-mediated electrophilic cyclization of 2-alkynyl-1,1'-biphenyls for the divergent synthesis of angular, bent, and zigzag fused nonplanar conjugated organic molecules was realized. The key feature of this reaction is a Wagner-Meerwein-type rearrangement via a spiro carbocation intermediate, which was formed by electrophilic cyclization of the 9 H -fluoren-9-one derivative at the meta position. The products can be advanced to helical fluorenes, which exhibit high fluorescence quantum yields.
Keyphrases
  • energy transfer
  • machine learning
  • molecular dynamics
  • photodynamic therapy
  • water soluble
  • single molecule
  • polycyclic aromatic hydrocarbons