Crucial role of elusive isomeric eta-complexes in gas-phase electrophilic aromatic alkylations.

@article{Marcantoni2005CrucialRO,
  title={Crucial role of elusive isomeric eta-complexes in gas-phase electrophilic aromatic alkylations.},
  author={Enrico Marcantoni and Graziella Roselli and Laura Lucarelli and Gabriele Renzi and Antonello Filippi and Cristiano Trionfetti and M. G. Speranza},
  journal={The Journal of organic chemistry},
  year={2005},
  volume={70 10},
  pages={4133-41}
}
[isomers: see text] The kinetics and stereochemistry of the protonation-induced unimolecular isomerization of (R)-1-D1-3-(p-fluorophenyl)butane have been investigated in the gas phase at 40-100 degrees C and 70-760 Torr. This process leads to the formation of the relevant meta and ortho isomers with partial racemization of the migrating sec-butyl moiety. Complete racemization is observed, instead, when the isomerization reaction involves a 1,2-H shift in the moving alkyl group. These results… CONTINUE READING