Synthesis of <i>anti</i>-[1](1,6)Naphthaleno[1](1,6)naphthalenophane by Double Contractive Annulation of [2.2]Paracyclophane
Sourav Biswas, Zahra A. Tabasi, Louise N. Dawe, Yuming Zhao, Graham J. Bodwell
Abstract
Two-directional contractive annulation of [2.2]paracyclophane has led to the synthesis of anti-[1](1,6)naphthaleno[1](1,6)naphthalenophane (3). This [1.1]cyclophane (SE = 56.6 kcal/mol) consists of two bent and twisted naphthalene units with interplanar distances as short as 2.74 Å. Despite the high strain and structural distortion, 3 was found to be unreactive toward potential cycloaddition partners (TCNE, DMAD) and under UV irradiation.
Topics & Concepts
AnnulationChemistryBent molecular geometryNaphthaleneCyclophaneCycloadditionDistortion (music)StereochemistryStrain (injury)CrystallographyMedicinal chemistryCrystal structureOrganic chemistryCatalysisElectronic engineeringEngineeringCMOSMedicineAmplifierInternal medicineSynthesis and Properties of Aromatic CompoundsDNA and Nucleic Acid ChemistryPhotochromic and Fluorescence Chemistry