title: Seleniranium ion-triggered reactions: new aspects of Friedel-Crafts and N-detosylative cyclizations.
abstract: Seleniranium ions at low temperatures (-90 to -78 degrees C) will initiate effective Friedel-Crafts cyclization if a suitably placed arene is allowed to react even when the arene is unactivated. These intermediates generated from N-aryl-N-tosylamides undergo a novel, surprisingly efficient, detosylative cyclization to form 5- or 6-membered nitrogen heterocycles. A debenzylation route is preferred if both benzyl and tosyl groups are present in the substrate.
authors.affiliation: Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.
authors.forename: Hwan Jung
authors.initials: HJ
authors.lastname: Lim
authors.forename: T V
authors.initials: TV
authors.lastname: RajanBabu
mesh_terms: D001393:Azoles / Q000737:chemistry; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003080:Cold Temperature; D003500:Cyclization; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D001393:Azoles; D001555:Benzene Derivatives; D016566:Organoselenium Compounds