Stereoselective synthesis of [2.2]triphenylenophanes<i>via</i>intramolecular double [2 + 2 + 2] cycloadditions
Yuya Kawai, Juntaro Nogami, Yuki Nagashima, Ken Tanaka
Abstract
the high-yielding base-mediated intermolecular macrocyclization and Rh- or Ni-catalyzed intramolecular double [2 + 2 + 2] cycloadditions. DFT calculations have revealed that the second [2 + 2 + 2] cycloaddition kinetically determines the diastereoselectivity. Single crystal X-ray diffraction analyses have confirmed that the facing triphenylene or [5]helicene skeletons strongly repel each other, resulting in curved structures with bulged centers.
Topics & Concepts
Intramolecular forceStereoselectivityChemistryStereochemistryCombinatorial chemistryOrganic chemistryCatalysisSynthesis and Properties of Aromatic CompoundsPhotochromic and Fluorescence ChemistryPorphyrin and Phthalocyanine Chemistry