title: On the reaction of 1,3-diphenylisobenzofuran and (2-iodoethynyl)(phenyl)iodonium triflate. A unique case of oxygen transfer from the Diels-Alder adduct to the diene.
abstract: Reaction of 1,3-diphenylisobenzofuran (DPIBF) with 2-(iodoethynyl)(phenyl)-iodonium triflate at room temperature gave the expected Diels-Alder adduct, but using an excess of DFIBF (2 equiv.) and performing the reaction at 55 °C or heating at this temperature during the concentration stage, the initial orange solution or product mixture became dark brown and the products 1,2-phenylene-1,2-bis(phenylmethanone) and 2-(3-iodo-1,4-diphenylnaphthyl)(phenyl)iodonium triflate were obtained, which suggests an oxygen transfer between DPIBF and the initial adduct.
authors: Pharmaceutical Chemistry Laboratory (CSIC Associated Unity), Biomedicine Institute of the University of Barcelona, University of Barcelona, Joan XXIII av., Barcelona E-08028, Spain. camps@ub.edu
authors: Pelayo
authors: P
authors: Camps
authors: Tània
authors: T
authors: Gómez
authors: David
authors: D
authors: Lozano
authors: Teresa
authors: T
authors: Calvet
authors: Mercè
authors: M
authors: Font-Bardia
mesh_terms: D001572:Benzofurans / Q000737:chemistry*; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D008698:Mesylates / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*
chemical_list: C576545:(2-iodoethynyl)(phenyl)iodonium triflate; D001572:Benzofurans; D008698:Mesylates; D009281:Naphthalenes; C011238:1,3-diphenylisobenzofuran; D010100:Oxygen