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Special Issue "Organic Iodine Chemistry 2012"

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A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 August 2012)

Special Issue Editor

Guest Editor
Dr. Bimal K. Banik

Vice President, Research & Education Development, Community Health Systems of South Texas, 3135 S. Sugar Road Edinburg, Texas 78539, USA
Fax: +1 956 384 5006
Interests: organic synthesis, medicinal chemistry, beta lactams, polyaromatic compounds, catalysis, microwave-induced reactions, and synthetic methods

Special Issue Information

Dear Colleagues,

In recent years, a large number of organic reactions have been reported using molecular iodine as catalyst and consequently "Organo-iodine chemistry" is considered as an emerging field of modern synthetic organic chemistry. Iodine is an inexpensive weak Lewis acid, readily available and easy-to-handle reagent for various organic transformations and yields products with outstanding selectivity and excellent yields. There is a growing trend of using iodine in organic synthesis. Molecules, a widely distributed journal of organic chemistry has planned to publish a Special Issue emphasizing "Organo-iodine chemistry". As a Guest Editor of this Special Issue it gives me immense pleasure to welcome iodine-mediated research works and reviews from academic and industrial scientists.

The main objective of this issue will be to provide useful information to researchers and students who are interested in the chemistry of iodine and its fascinating role in organic synthesis. Efforts will be made to include not only the synthesis of organic compounds but also to understand the mechanism of iodine-mediated reactions under different conditions.

I believe this Special Issue on "Organo-iodine chemistry" will offer a world-wide forum to present original research works and reviews focused on the synthesis of organic compounds especially, molecules of biological interest, using a variety of novel and eco-friendly strategies.  I also hope that this issue will reflect the innovation and diversity of this growing field of "Organo-iodine chemistry".

Prof. Dr. Bimal K. Banik
Guest Editor

Keywords

  • iodine
  • organic synthesis
  • mechanism
  • biologically active compounds
  • catalysis
  • eco-friendly reactions

Published Papers (3 papers)

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Research

Open AccessCommunication Radioiodination of Aryl-Alkyl Cyclic Sulfates
Molecules 2012, 17(11), 13266-13274; doi:10.3390/molecules171113266
Received: 7 September 2012 / Revised: 24 September 2012 / Accepted: 23 October 2012 / Published: 7 November 2012
Cited by 1 | PDF Full-text (217 KB) | Supplementary Files
Abstract
Among the currently available positron emitters suitable for Positron Emission Tomography (PET), 124I has the longest physical half-life (4.2 days). The long half-life and well-investigated behavior of iodine in vivo makes 124I very attractive for pharmacological studies. In this communication, [...] Read more.
Among the currently available positron emitters suitable for Positron Emission Tomography (PET), 124I has the longest physical half-life (4.2 days). The long half-life and well-investigated behavior of iodine in vivo makes 124I very attractive for pharmacological studies. In this communication, we describe a simple yet effective method for the synthesis of novel 124I labeled compounds intended for PET imaging of arylsulfatase activity in vivo. Arylsulfatases have important biological functions, and genetic deficiencies of such functions require pharmacological replacement, the efficacy of which must be properly and non-invasively evaluated. These enzymes, even though their natural substrates are mostly of aliphatic nature, hydrolyze phenolic sulfates to phenol and sulfuric acid. The availability of [124I]iodinated substrates is expected to provide a PET-based method for measuring their activity in vivo. The currently available methods of synthesis of iodinated arylsulfates usually require either introducing of a protected sulfate ester early in the synthesis or introduction of sulfate group at the end of synthesis in a separate step. The described method gives the desired product in one step from an aryl-alkyl cyclic sulfate. When treated with iodide, the source cyclic sulfate opens with substitution of iodide at the alkyl center and gives the desired arylsulfate monoester. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry 2012)
Open AccessArticle 17O-Dynamic NMR and DFT Investigation of Bis(acyloxy)iodoarenes
Molecules 2012, 17(11), 12718-12733; doi:10.3390/molecules171112718
Received: 11 September 2012 / Revised: 10 October 2012 / Accepted: 19 October 2012 / Published: 26 October 2012
Cited by 3 | PDF Full-text (754 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Bis(acetoxy)iodobenzene and related acyloxy derivatives of hypervalent I(III) were studied by variable temperature solution-state 17O-NMR and DFT calculations. The 17O-NMR spectra reveal a dynamic process that interchanges the oxygen atoms of the acyloxy groups. For the first time, coalescence events [...] Read more.
Bis(acetoxy)iodobenzene and related acyloxy derivatives of hypervalent I(III) were studied by variable temperature solution-state 17O-NMR and DFT calculations. The 17O-NMR spectra reveal a dynamic process that interchanges the oxygen atoms of the acyloxy groups. For the first time, coalescence events could be detected for such compounds, allowing the determination of activation free energy data which are found to range between 44 and 47 kJ/mol. The analysis of the 17O linewidth measured for bis(acetoxy)iodobenzene indicates that the activation entropy is negligible. DFT calculations show that the oxygen atom exchange arises as a consequence of the [1,3]-sigmatropic shift of iodine. The calculated activation barriers are in excellent agreement with the experimental results. Both the 17O-NMR and DFT studies show that the solvent and chemical alterations, such as modification of the acyl groups or para- substitution of the benzene ring, hardly affect the energetics of the dynamic process. The low I-O Wiberg bond index (0.41–0.42) indicates a possible explanation of the invariance of both the energy barrier and the 17O chemical shift with para-substitution. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry 2012)
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Open AccessArticle Synthesis of Highly Substituted Oxazoles through Iodine(III)-Mediated Reactions of Ketones with Nitriles
Molecules 2012, 17(9), 11046-11055; doi:10.3390/molecules170911046
Received: 6 August 2012 / Revised: 29 August 2012 / Accepted: 10 September 2012 / Published: 13 September 2012
Cited by 7 | PDF Full-text (260 KB)
Abstract In the presence of trifluoromethanesulfonic acid (TfOH) or bis(trifluoromethane-sulfonyl)imide (Tf2NH), iodosobenzene (PhI=O) efficiently promoted the reactions of dicarbonyl compounds as well as monocarbonyl compounds with nitriles to give 2,4-disubstituted and 2,4,5-trisubstituted oxazole in a single step under the mild conditions. Full article
(This article belongs to the Special Issue Organic Iodine Chemistry 2012)
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