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Four‐Center Two‐Electron Bonding in a Tetrahedral Topology. Experimental Realization of Three‐Dimensional Homoaromaticity in the 1,3‐Dehydro‐5,7‐adamantanediyl Dication

1987; Wiley; Volume: 26; Issue: 8 Linguagem: Inglês

10.1002/anie.198707611

1521-3773

Matthias Bremer, Paul von Ragué Schleyer, Karl Schötz, M. Kausch, Michael Schindler,

Molecular spectroscopy and chirality

Angewandte Chemie International Edition in EnglishVolume 26, Issue 8 p. 761-763 Communication Four-Center Two-Electron Bonding in a Tetrahedral Topology. Experimental Realization of Three-Dimensional Homoaromaticity in the 1,3-Dehydro-5,7-adamantanediyl Dication†‡ Dipl.-Chem. Matthias Bremer, Dipl.-Chem. Matthias Bremer Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)Search for more papers by this authorProf. Dr. Paul von Ragué Schleyer, Corresponding Author Prof. Dr. Paul von Ragué Schleyer Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)Search for more papers by this authorDr. Karl Schötz, Dr. Karl Schötz Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)Search for more papers by this authorDr. Michael Kausch, Dr. Michael Kausch Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)Search for more papers by this authorDr. Michael Schindler, Dr. Michael Schindler Lehrstuhl für Theoretische Chemie der Universität, Postfach 10 2148, D-4630 Bochum 1 (FRG)Search for more papers by this author Dipl.-Chem. Matthias Bremer, Dipl.-Chem. Matthias Bremer Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)Search for more papers by this authorProf. Dr. Paul von Ragué Schleyer, Corresponding Author Prof. Dr. Paul von Ragué Schleyer Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)Search for more papers by this authorDr. Karl Schötz, Dr. Karl Schötz Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)Search for more papers by this authorDr. Michael Kausch, Dr. Michael Kausch Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-8520 Erlangen (FRG)Search for more papers by this authorDr. Michael Schindler, Dr. Michael Schindler Lehrstuhl für Theoretische Chemie der Universität, Postfach 10 2148, D-4630 Bochum 1 (FRG)Search for more papers by this author First published: August 1987 https://doi.org/10.1002/anie.198707611Citations: 69 † We thank the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie, ARDEC, Dover, NJ, and the CONVEX Corporation (the most recent calculations were carried out on a CONVEX Cl computer) for support, Dr. Alan Reed (Erlangen) for discussions, and Dr. W. Bauer (Erlangen) for the NMR spectra. ‡ Dedicated to Professor George A. Olah on the occasion of his 60th birthday AboutPDF 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 A nonclassical structure for the dication 3 is supported, in particular, by the 13C-NMR data: the signals of the bridgehead C atoms are shifted upfield (δ = 6.6) and not downfield, as would have been expected for a classical dication. The resonances of the methylene C atoms are observed at δ = 35.6 (1H-NMR: δ = 3.8). Compound 3 is synthesized starting from 1,3,5,7-tetra-iodoadamantane, which reacts with HgF2 to give 1. Compound 1 reacts with nBuLi to give 2, from which 3 can be generated. The dication 3 is stable up to 0°C. Citing Literature Volume26, Issue8August 1987Pages 761-763 RelatedInformation