Literature DB >> 27766886

Reactions of HDDA-Derived Benzynes with Perylenes: Rapid Construction of Polycyclic Aromatic Compounds.

Feng Xu1, Xiao Xiao1, Thomas R Hoye1.   

Abstract

Benzynes produced by the thermal cycloisomerization of tetrayne substrates [i.e., by the hexadehydro-Diels-Alder (HDDA) reaction] react with perylenes to produce novel naphthoperylene derivatives. Cyclic voltammetry and absorption and emission properties of these compounds are described. DFT studies shed additional light on the dearomatization that accompanies the reaction as well as some of the spectroscopic behavior.

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Year:  2016        PMID： 27766886      PMCID： PMC5107110          DOI： 10.1021/acs.orglett.6b02878

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  Noncovalent functionalization, exfoliation, and solubilization of graphene in water by employing a fluorescent coronene carboxylate.

Authors:  Anupama Ghosh; K Venkata Rao; Subi J George; C N R Rao
Journal:  Chemistry       Date:  2010-03-01       Impact factor: 5.236

2.  Synthesis of complex benzenoids via the intermediate generation of o-benzynes through the hexadehydro-Diels-Alder reaction.

Authors:  Beeraiah Baire; Dawen Niu; Patrick H Willoughby; Brian P Woods; Thomas R Hoye
Journal:  Nat Protoc       Date:  2013-02-14       Impact factor: 13.491

3.  From perylene to a 22-ring aromatic hydrocarbon in one-pot.

Authors:  Bruno Schuler; Sara Collazos; Leo Gross; Gerhard Meyer; Dolores Pérez; Enrique Guitián; Diego Peña
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-01       Impact factor: 15.336

4.  Perylene, Oligorylenes, and Aza-Analogs.

Authors:  John T Markiewicz; Fred Wudl
Journal:  ACS Appl Mater Interfaces       Date:  2015-10-23       Impact factor: 9.229

5.  Mechanistic Insight into the Dehydro-Diels-Alder Reaction of Styrene-Ynes.

Authors:  Laura S Kocsis; Husain N Kagalwala; Sharlene Mutto; Bhaskar Godugu; Stefan Bernhard; Dean J Tantillo; Kay M Brummond
Journal:  J Org Chem       Date:  2015-03-02       Impact factor: 4.354

6.  The hexadehydro-Diels-Alder reaction.

Authors:  Thomas R Hoye; Beeraiah Baire; Dawen Niu; Patrick H Willoughby; Brian P Woods
Journal:  Nature       Date:  2012-10-11       Impact factor: 49.962
  6 in total
  3 in total

Review 1.  Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.

Authors:  Lucas L Fluegel; Thomas R Hoye
Journal:  Chem Rev       Date:  2021-01-25       Impact factor: 60.622

2.  The domino hexadehydro-Diels-Alder reaction transforms polyynes to benzynes to naphthynes to anthracynes to tetracynes (and beyond?).

Authors:  Xiao Xiao; Thomas R Hoye
Journal:  Nat Chem       Date:  2018-07-20       Impact factor: 24.427

Review 3.  Diels-Alder Cycloaddition to the Bay Region of Perylene and Its Derivatives as an Attractive Strategy for PAH Core Expansion: Theoretical and Practical Aspects.

Authors:  Aneta Kurpanik; Marek Matussek; Piotr Lodowski; Grażyna Szafraniec-Gorol; Michał Krompiec; Stanisław Krompiec
Journal:  Molecules       Date:  2020-11-17       Impact factor: 4.411
  3 in total

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