Valence Isomerization of syn ‐Benzene Trioxide to cis,cis,cis ‐1,4,7‐Trioxacyclononatriene; anti ‐Benzene Trioxide
1972; Wiley; Volume: 11; Issue: 10 Linguagem: Italiano
10.1002/anie.197209391
ISSN1521-3773
AutoresEmanuel Vogel, Hans‐Josef Altenbach, Claus‐Dieter Sommerfeld,
Tópico(s)Chemistry and Chemical Engineering
ResumoAngewandte Chemie International Edition in EnglishVolume 11, Issue 10 p. 939-940 Communication Valence Isomerization of syn-Benzene Trioxide to cis,cis,cis-1,4,7-Trioxacyclononatriene; anti-Benzene Trioxide† Prof. Dr. Emanuel Vogel, Prof. Dr. Emanuel Vogel Institut für Organische Chemie der Universität, 5 Köln 1, Zülpicher Strasse 47 (Germany)Search for more papers by this authorDipl.-Chem. Hans-Josef Altenbach, Dipl.-Chem. Hans-Josef Altenbach Institut für Organische Chemie der Universität, 5 Köln 1, Zülpicher Strasse 47 (Germany)Search for more papers by this authorClaus-Dieter Sommerfeld, Corresponding Author Claus-Dieter Sommerfeld Institut für Organische Chemie der Universität, 5 Köln 1, Zülpicher Strasse 47 (Germany)Institut für Organische Chemie der Universität, 5 Köln 1, Zülpicher Strasse 47 (Germany)Search for more papers by this author Prof. Dr. Emanuel Vogel, Prof. Dr. Emanuel Vogel Institut für Organische Chemie der Universität, 5 Köln 1, Zülpicher Strasse 47 (Germany)Search for more papers by this authorDipl.-Chem. Hans-Josef Altenbach, Dipl.-Chem. Hans-Josef Altenbach Institut für Organische Chemie der Universität, 5 Köln 1, Zülpicher Strasse 47 (Germany)Search for more papers by this authorClaus-Dieter Sommerfeld, Corresponding Author Claus-Dieter Sommerfeld Institut für Organische Chemie der Universität, 5 Köln 1, Zülpicher Strasse 47 (Germany)Institut für Organische Chemie der Universität, 5 Köln 1, Zülpicher Strasse 47 (Germany)Search for more papers by this author First published: October 1972 https://doi.org/10.1002/anie.197209391Citations: 83 † The first report of our syntheses of syn- and anti-benzene trioxide (1) and (6) was made by E. Vogel at a seminar in Freiburg arranged by Professor H. Prinzbach on July 11, 1972. The synthetic methods, melting points and NMR spectra of the two compounds were included in a previous paper [1] received on July 28, 1972. 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 onEmailFacebookTwitterLinkedInRedditWechat No abstract is available for this article. References 1 H.-J. Altenbach and E. Vogel, Angew. Chem. 84, 985 (1972); 10.1002/ange.19720842005 Google Scholar Angew. Chem. internat. Edit. 11, 937 (1972). 10.1002/anie.197209371 CASWeb of Science®Google Scholar 2 Review: F. Vogel and H. Günther, Angew. Chem. 79, 429 (1967); 10.1002/ange.19670791002 Google Scholar Angew. Chem. internal. Edit. 6, 385 (1967). 10.1002/anie.196703851 CASGoogle Scholar 3 E. Vogel, H.-J. Altenbach, and D. Cremer, Angew. Chem. 84, 983 (1972); 10.1002/ange.19720842004 Google Scholar Angew. Chem. internat. Edit. 11, 935 (1972). 10.1002/anie.197209351 CASWeb of Science®Google Scholar 4 R. B. Woodward, T. Fukunaga, and R. C. Kelley, J. Amer. Chem. Soc. 86, 3162 (1964). 10.1021/ja01069a046 CASGoogle Scholar 5 For the synthesis of triquinacene see also: A. de Meijere, D. Kaufmann, and O. Schallner, Angew. Chem. 83, 404 (1971); 10.1002/ange.19710831110 Google Scholar Angew. Chem. internat. Edit. 10, 417 (1971). 10.1002/anie.197104171 CASGoogle Scholar 6 R. B. Woodward and R. Hoffmann: The Conservation of Orbital Symmetry, Verlag Chemie, Weinheim 1970, p. 101. Google Scholar 7 H. Prinzbach and D. Stusche, Angew. Chem. 82, 836 (1970); 10.1002/ange.19700822007 Google Scholar Angew. Chem. internat. Edit. 9, 799 (1970); 10.1002/anie.197007991 CASWeb of Science®Google Scholar H. Prinzbach and D. Stusche, Helv. Chim. Acta 54, 755 (1971); 10.1002/hlca.19710540234 CASWeb of Science®Google Scholar H. W. Whitlock Jr., and P. F. Schatz, J. Amer. Chem. Soc. 93, 3837 (1971); 10.1021/ja00744a086 CASWeb of Science®Google Scholar D. L. Dalrymple and S. P. B. Taylor, J. Amer. Chem. Soc. 93, 7098 (1971). 10.1021/ja00754a074 CASWeb of Science®Google Scholar 8 The anti-trishomobenzene corresponding to (6) was very recently described by M. Engelhard and W. Lüttke, Angew. Chem. 84, 346 (1972); 10.1002/ange.19720840807 Google Scholar Angew. Chem. internat. Edit 11, 310 (1972). 10.1002/anie.197203101 CASGoogle Scholar 9 Examples of thermal rearrangements of endo-peroxides to syn-diepoxides have been provided by K. H. Schulte-Elte, B. Willhalm, and G. Ohloff, Angew. Chem. 81, 1045 (1969); 10.1002/ange.19690812406 Google Scholar Angew. Chem. internat. Edit. 8, 985 (1969); 10.1002/anie.196909851 CASWeb of Science®Google Scholaralso K. K. Maheshwari, P. de Mayo, and D. Wiegand, Can. J. Chem. 48, 3265 (1970). 10.1139/v70-548 CASWeb of Science®Google Scholar 10 K. Gollnick and G. O. Schenck in J. Hamer: 1,4-Cycloaddition Reactions. Academic Press, New York 1967, p. 286. Google Scholar 11 Irradiation was effected with a sodium vapor lamp (Philips 57016 P 50 I, 60 W) in order to avoid the photoisomerization of oxepin to 2-oxabicyclo[3.2.0]hepta-3,6-diene caused by UV light. Google Scholar 12 C. J. Pedersen and H. K. Frensdorff, Angew. Chem. 84, 16 (1972); 10.1002/ange.19720840104 CASWeb of Science®Google Scholar Angew. Chem. internat. Edit. 11, 16 (1972). 10.1002/anie.197200161 CASPubMedWeb of Science®Google Scholar Citing Literature Volume11, Issue10October 1972Pages 939-940 ReferencesRelatedInformation
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