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

Article abstract of DOI:10.3390/molecules17088795

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.