Next Article in Journal
Comparison on Phenolic Compounds and Antioxidant Properties of Cabernet Sauvignon and Merlot Wines from Four Wine Grape-Growing Regions in China
Next Article in Special Issue
On the Catalytic Effect of Water in the Intramolecular Diels–Alder Reaction of Quinone Systems: A Theoretical Study
Previous Article in Journal
Investigation of Non-Enzymatic Glycosylation of Human Serum Albumin Using Ion Trap-Time of Flight Mass Spectrometry
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)
View Full-Text   |   Download PDF [380 KB, uploaded 18 June 2014]   |  

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 (CC BY 3.0).

Supplementary material

SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert