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Molecules 2012, 17(8), 8795-8803; doi:10.3390/molecules17088795
Communication

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

1,* , 1
, 1
, 2
 and 2,3
1 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 2 Crystallography, Mineralogy and Mineral Deposits, University of Barcelona, Martí Franquès st., Barcelona E-08028, Spain 3 X-ray Diffraction Unity, Scientific and Technologic Centre of the University of Barcelona (CCiTUB), University of Barcelona, Solé i Sabarís st. 1–3, Barcelona E-08028, Spain
Dedicated to Professor Miguel Angel Miranda on the occasion of his 60th birthday.
* Author to whom correspondence should be addressed.
Received: 13 June 2012 / Revised: 26 June 2012 / Accepted: 10 July 2012 / Published: 25 July 2012
(This article belongs to the Special Issue Diels-Alder Reaction)
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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.
Keywords: NMR spectroscopy; structure elucidation; X-ray diffraction NMR spectroscopy; structure elucidation; X-ray diffraction
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Camps, P.; Gómez, T.; Lozano, D.; Calvet, T.; Font-Bardia, M. 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 2012, 17, 8795-8803.

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