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Special Issue "Diels-Alder Reaction"

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

Deadline for manuscript submissions: closed (31 December 2012)

Special Issue Editor

Guest Editor
Prof. Dr. Raymond J. Giguere (Website)

Department of Chemistry, Skidmore College, 815 N. Broadway, Saratoga Springs, NY 12866, USA
Interests: intramolecular cycloadditions; microwave heating in organic synthesis; public perception of natural science

Special Issue Information

Dear Colleagues,

The Diels-Alder reaction, discovered in 1928, is widely recognized as one of the cornerstone synthetic organic reactions of the 20th century. In fact, it is one of the most commonly employed reactions for the synthesis of natural products, as well as for the rapid construction of cyclic and polycyclic compounds. The intramolecular extension of the Diels-Alder, first reported by Kurt Alder in 1952, led the way to a significant number of elegant synthetic achievements. Further historical developments (e.g., Lewis acid catalysis, frontier orbital theory, introduction of heteroatoms, comprehension of stereoelectronic features, solvent and temperature effects, the use of high pressure or microwave heating conditions, etc.) involving this Nobel-prize winning reaction have made the Diels-Alder reaction an efficient, reliable and powerful tool in the hands of synthetic chemists everywhere.

Molecules Special Issue on Diels-Alder chemistry will provide a timely venue for presenting key developments and important facets of this milestone reaction. I strongly encourage authors to submit papers for this Special Issue, and am hopeful that the topics published will assist in promoting novel applications of this exceptional process for the synthesis of organic molecules of interest and importance.

Prof. Raymond J. Giguere, 
Guest Editor

Keywords

  • Diels-Alder Reaction
  • Hetero Diels-Alder
  • IMDA
  • cycloaddition
  • [4 + 2]
  • diene
  • dienophile
  • endo
  • exo

Published Papers (4 papers)

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Research

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Open AccessArticle Growth of Fullerene Fragments Using the Diels-Alder Cycloaddition Reaction: First Step towards a C60 Synthesis by Dimerization
Molecules 2013, 18(2), 2243-2254; doi:10.3390/molecules18022243
Received: 25 December 2012 / Revised: 20 January 2013 / Accepted: 5 February 2013 / Published: 13 February 2013
Cited by 3 | PDF Full-text (576 KB)
Abstract
Density Functional Theory has been used to model the Diels-Alder reactions of the fullerene fragments triindenetriphenilene and pentacyclopentacorannulene with ethylene and 1,3-butadiene. The purpose is to prove the feasibility of using Diels-Alder cycloaddition reactions to grow fullerene fragments step by step, and [...] Read more.
Density Functional Theory has been used to model the Diels-Alder reactions of the fullerene fragments triindenetriphenilene and pentacyclopentacorannulene with ethylene and 1,3-butadiene. The purpose is to prove the feasibility of using Diels-Alder cycloaddition reactions to grow fullerene fragments step by step, and to dimerize fullerene fragments, as a way to obtain C60. The dienophile character of the fullerene fragments is dominant, and the reaction of butadiene with pentacyclopentacorannulene is favored. Full article
(This article belongs to the Special Issue Diels-Alder Reaction)
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Open AccessArticle On the Catalytic Effect of Water in the Intramolecular Diels–Alder Reaction of Quinone Systems: A Theoretical Study
Molecules 2012, 17(11), 13687-13703; doi:10.3390/molecules171113687
Received: 18 September 2012 / Revised: 8 November 2012 / Accepted: 12 November 2012 / Published: 20 November 2012
Cited by 8 | PDF Full-text (454 KB) | Supplementary Files
Abstract
The mechanism of the intramolecular Diels–Alder (IMDA) reaction of benzoquinone 1, in the absence and in the presence of three water molecules, 1w, has been studied by means of density functional theory (DFT) methods, using the M05-2X and B3LYP functionals for exploration [...] Read more.
The mechanism of the intramolecular Diels–Alder (IMDA) reaction of benzoquinone 1, in the absence and in the presence of three water molecules, 1w, has been studied by means of density functional theory (DFT) methods, using the M05-2X and B3LYP functionals for exploration of the potential energy surface (PES). The energy and geometrical results obtained are complemented with a population analysis using the NBO method, and an analysis based on the global, local and group electrophilicity and nucleophilicity indices. Both implicit and explicit solvation emphasize the increase of the polarity of the reaction and the reduction of activation free energies associated with the transition states (TSs) of this IMDA process. These results are reinforced by the analysis of the reactivity indices derived from the conceptual DFT, which show that the increase of the electrophilicity of the quinone framework by the hydrogen-bond formation correctly explains the high polar character of this intramolecular process. Large polarization at the TSs promoted by hydrogen-bonds and implicit solvation by water together with a high electrophilicity-nucleophilicity difference consistently explains the catalytic effects of water molecules. Full article
(This article belongs to the Special Issue Diels-Alder Reaction)
Open AccessCommunication 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(8), 8795-8803; doi:10.3390/molecules17088795
Received: 13 June 2012 / Revised: 26 June 2012 / Accepted: 10 July 2012 / Published: 25 July 2012
PDF Full-text (380 KB) | HTML Full-text | XML Full-text | Supplementary Files
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Diels-Alder Reaction)
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Review

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Open AccessReview Diels-Alder Reactions of 12-Hydroxy-9(10®20)-5aH-abeo-abieta-1(10),8(9),12(13)-triene-11,14-dione
Molecules 2013, 18(6), 6969-6989; doi:10.3390/molecules18066969
Received: 1 March 2013 / Revised: 14 May 2013 / Accepted: 30 May 2013 / Published: 14 June 2013
Cited by 2 | PDF Full-text (497 KB) | HTML Full-text | XML Full-text
Abstract
12-Hydroxy-9(10®20)-5aH-abeo-abieta-1(10),8(9),12(13)-triene-11,14-dione (quinone 2) served as the dienophile in numerous intermolecular Diels-Alder reactions. These cycloadditions were conducted either thermally (including microwave heating) or with Lewis acid activation. While most dienes reacted with quinone 2 in good chemical yield, others were incompatible under [...] Read more.
12-Hydroxy-9(10®20)-5aH-abeo-abieta-1(10),8(9),12(13)-triene-11,14-dione (quinone 2) served as the dienophile in numerous intermolecular Diels-Alder reactions. These cycloadditions were conducted either thermally (including microwave heating) or with Lewis acid activation. While most dienes reacted with quinone 2 in good chemical yield, others were incompatible under the experimental conditions used. Full article
(This article belongs to the Special Issue Diels-Alder Reaction)
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