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The Generation of Aryl Anions by Double Electron Transfer to Aryl Iodides from a Neutral Ground‐State Organic Super‐Electron Donor

2007; Wiley; Volume: 46; Issue: 27 Linguagem: Inglês

10.1002/anie.200700554

1521-3773

John A. Murphy, Shengze Zhou, Douglas W. Thomson, Franziska Schoenebeck, Mohan Mahesh, Stuart R. Park, Tell Tuttle, L.E.A. Berlouis,

Advanced Chemical Physics Studies

Angewandte Chemie International EditionVolume 46, Issue 27 p. 5178-5183 Communication The Generation of Aryl Anions by Double Electron Transfer to Aryl Iodides from a Neutral Ground-State Organic Super-Electron Donor† John A. Murphy Prof. Dr., John A. Murphy Prof. Dr. john.murphy@strath.ac.uk WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this authorSheng-ze Zhou Dr., Sheng-ze Zhou Dr. WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this authorDouglas W. Thomson, Douglas W. Thomson WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this authorFranziska Schoenebeck, Franziska Schoenebeck WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this authorMohan Mahesh Dr., Mohan Mahesh Dr. WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this authorStuart R. Park, Stuart R. Park WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this authorTell Tuttle Dr., Tell Tuttle Dr. tell.tuttle@strath.ac.uk WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this authorLeonard E. A. Berlouis Dr., Leonard E. A. Berlouis Dr. WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this author John A. Murphy Prof. Dr., John A. Murphy Prof. Dr. john.murphy@strath.ac.uk WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this authorSheng-ze Zhou Dr., Sheng-ze Zhou Dr. WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this authorDouglas W. Thomson, Douglas W. Thomson WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this authorFranziska Schoenebeck, Franziska Schoenebeck WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this authorMohan Mahesh Dr., Mohan Mahesh Dr. WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this authorStuart R. Park, Stuart R. Park WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this authorTell Tuttle Dr., Tell Tuttle Dr. tell.tuttle@strath.ac.uk WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this authorLeonard E. A. Berlouis Dr., Leonard E. A. Berlouis Dr. WestCHEM, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK, Fax: (+44) 548-4246Search for more papers by this author First published: 22 June 2007 https://doi.org/10.1002/anie.200700554Citations: 112 † We thank the EPRSC (S.Z.Z., D.W.T., F.S., and S.R.P.), the CVCP (Universities UK), and the University of Strathclyde (M.M.) for funding, the EPRSC National Mass Spectrometry Service Centre, Swansea for mass spectra, and Dr. K. Daasbjerg for helpful discussions. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract It takes two to cyclize: Aryl halides are reduced to aryl anions by double electron transfer from the neutral ground-state electron donor 1 (see scheme), as shown by the formation of a cyclic ketone (2). The reduced compound (3) is also formed. Calculations show that the loss of two electrons from 1 is both thermodynamically and kinetically viable and generates a more planar resonance-stabilized structure. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z700554_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume46, Issue27July 2, 2007Pages 5178-5183 RelatedInformation