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One-Pot Synthesis and Conformational Analysis of Six-Membered Cyclic Iodonium Salts.

Lucien D CaspersJulian SpilsMattis DamrathEnno LorkBoris J Nachtsheim
Published in: The Journal of organic chemistry (2020)
Two one-pot procedures for the construction of carbon-bridged diaryliodonium triflates and tetrafluoroborates are described. Strong Brønsted acids enable the effective Friedel-Crafts alkylation with diversely substituted o-iodobenzyl alcohol derivatives, providing diphenylmethane scaffolds, which are subsequently oxidized and cyclized to the corresponding dibenzo[b,e]iodininium salts. Based on NMR investigations and density functional theory (DFT) calculations, we could verify the so-far-undescribed existence of two stable isomers in cyclic iodonium salts substituted with aliphatic side chains in the carbon bridge.
Keyphrases
  • density functional theory
  • molecular dynamics
  • ionic liquid
  • molecular docking
  • molecular dynamics simulations
  • magnetic resonance
  • high resolution
  • single molecule
  • tissue engineering
  • low density lipoprotein