The first example of a pseudo-ortho metallation on [2.2]paracyclophane is presented, giving easy access to enantiopure compounds of this type. By slight modification of the directing group, metallation of the ortho- and C2-positions is possible. The mechanism was further investigated by means of density functional theory (DFT) calculations.
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Macrocyclic Oligothiophene with Stereogenic [2.2]Paracyclophane Scaffolds: Chiroptical Properties from π-Transannular Interactions.
Chemistry
March 2017
Department of Chemistry, Graduate School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa, 252-0373, Japan.
The enantiomers of a new cyclic oligothiophene, bridged by two pseudo-ortho[2.2]paracyclophanes, were synthesized as a new class of the chiral π-conjugated system. Single-crystal X-ray diffraction analysis revealed a twisted structure for these oligothiophenes induced by a torsion of the cyclophane moieties.
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Chem Commun (Camb)
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Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
The first example of a pseudo-ortho metallation on [2.2]paracyclophane is presented, giving easy access to enantiopure compounds of this type. By slight modification of the directing group, metallation of the ortho- and C2-positions is possible.
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