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 †

Molecules

Pelayo Camps²  Tània Gómez²  David Lozano²  Teresa Calvet¹ 

[1] Crystallography, Mineralogy and Mineral Deposits, University of Barcelona, Martí Franquès st., Barcelona E-08028, Spain;Pharmaceutical Chemistry Laboratory (CSIC Associated Unity), Faculty of Pharmacy, Biomedicine Institute of the University of Barcelona (IBUB), University of Barcelona, Joan XXIII av., Barcelona E-08028, Spain;

关键词: NMR spectroscopy;    structure elucidation;    X-ray diffraction;   

DOI  :  10.3390/molecules17088795

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2012 by the authors; licensee MDPI, Basel, Switzerland.