Efficient synthesis and unit-selective π-extension of π-fused [4.3.3]propellane as a chiral building block
Kenichi Kato, Seigo Tanaka, Nobuyoshi Seto, Keisuke Wada, Masayuki Gon, Shixin Fa, Shunsuke Ohtani, Kazuo Tanaka, Tomoki Ogoshi
Abstract
A three-dimensional skeleton, π-fused [4.3.3]propellane, was constructed and derivatized by selective π-extension at the two naphthalene units. The obtained propellanes existed as stereoisomers different in spatial arrangement, one of which displayed a chiroptical response originating from through-space interactions between 5-azachrysenes in a skew position.
Topics & Concepts
PropellaneBlock (permutation group theory)Yield (engineering)Derivative (finance)ChemistryConjugated systemCombinatorial chemistryExtension (predicate logic)NaphthaleneUnit (ring theory)StereochemistryBicyclic moleculeOrganic chemistryMaterials scienceComputer scienceMathematicsCombinatoricsMetallurgyFinancial economicsMathematics educationPolymerProgramming languageEconomicsSynthesis and Properties of Aromatic CompoundsPorphyrin and Phthalocyanine ChemistryAxial and Atropisomeric Chirality Synthesis