title: Mild preparation of functionalized [2.2]paracyclophanes via the Pummerer rearrangement.
abstract: [2.2]Paracyclophanes, incorporating functional groups in the aliphatic bridges, suitable for elimination to give [2.2]paracyclophanedienes, are synthesized through a novel approach. It relies on a double Pummerer rearrangement on dithiacyclophane precursors, followed by ring contraction through a photochemical sulfur extrusion, and it is compatible with aryl moieties possessing very different electronic properties.
authors.affiliation: Department of Chemistry and INSTM Research Unit, University of Pavia, Viale Taramelli 10, 27100, Pavia, Italy.
authors.forename: Matteo
authors.initials: M
authors.lastname: Montanari
authors.forename: Alberto
authors.initials: A
authors.lastname: Bugana
authors.forename: Arvind K
authors.initials: AK
authors.lastname: Sharma
authors.forename: Dario
authors.initials: D
authors.lastname: Pasini
mesh_terms: D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy / Q000592:standards; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012015:Reference Standards; D013237:Stereoisomerism
chemical_list: D011083:Polycyclic Compounds; C515344:(2.2)paracyclophane