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- 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.
- Authors
Camps, Pelayo; Gómez, Tània; Lozano, David; Calvet, Teresa; Font-Bardia, Mercè
- 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.
- Subjects
DIELS-Alder reaction; TRIFLATE compounds; CHEMICAL reactions; TRIFLUOROMETHANESULFONYL compounds; BENZOFURAN
- Publication
Molecules, 2012, Vol 17, Issue 8, p8795
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules17088795