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

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
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
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

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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