title: Preparations of SF(5)- and CF(3)-substituted arenes utilizing the 7-oxabicyclo[2.2.1]hept-2-ene synthones.
abstract: The synthesis of SF5- and CF3-substituted benzenes and naphthalenes from various 7-oxanorbornene derivatives utilizing SF5Cl and CF3I radical addition reactions, followed by dehydrohalogenation and aromatization, is reported. The differences in the behavior of the SF5- and CF3-containing intermediates under basic and acidic conditions are discussed. The experimentally observed high regioselectivities of the formation of 2-RF-substituted-1-naphthols agree well with the ab initio computations, revealing the first example of the SF5···HO hydrogen bonding.
authors.affiliation: School of Engineering and Science, Jacobs University Bremen gGmbH, Campus Ring 1, 28759 Bremen, Germany. m.ponomarenko@jacobs-university.de.
authors.forename: Maxim V
authors.initials: MV
authors.lastname: Ponomarenko
authors.forename: Katrin
authors.initials: K
authors.lastname: Lummer
authors.forename: Andrey A
authors.initials: AA
authors.lastname: Fokin
authors.forename: Yurii A
authors.initials: YA
authors.lastname: Serguchev
authors.forename: Bassem S
authors.initials: BS
authors.lastname: Bassil
authors.forename: Gerd-Volker
authors.initials: GV
authors.lastname: Röschenthaler
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D005466:Fluorocarbons / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D011789:Quantum Theory; D013457:Sulfur Compounds / Q000737:chemistry*
chemical_list: D001555:Benzene Derivatives; D019086:Bridged Bicyclo Compounds, Heterocyclic; D005466:Fluorocarbons; D009281:Naphthalenes; D013457:Sulfur Compounds; C115613:sulfur pentafluoride cation; D005459:Fluorides