Methylenenorbornadiene, a Bicycloheptafulvene
1972; Wiley; Volume: 11; Issue: 6 Linguagem: Inglês
10.1002/anie.197205121
ISSN1521-3773
AutoresReinhard W. Hoffmann, Reinhard Schüttler, Werner Schäfer, Armin Schweig,
Tópico(s)Axial and Atropisomeric Chirality Synthesis
ResumoAngewandte Chemie International Edition in EnglishVolume 11, Issue 6 p. 512-513 Communication Methylenenorbornadiene, a Bicycloheptafulvene†‡ Prof. Dr. Reinhard W. Hoffmann, Prof. Dr. Reinhard W. Hoffmann Fachbereich Chemie der Universität, 355 Marburg, Lahnberge (Germany)Search for more papers by this authorDipl.-Chem. Reinhard Schüttler, Dipl.-Chem. Reinhard Schüttler Fachbereich Chemie der Universität, 355 Marburg, Lahnberge (Germany)Search for more papers by this authorDipl.-Chem. Werner Schäfer, Dipl.-Chem. Werner Schäfer Physikalisch-Chemisches Institut der Universität, 355 Marburg, Biegenstrasse 12 (Germany)Search for more papers by this authorProf. Dr. Armin Schweig, Corresponding Author Prof. Dr. Armin Schweig Physikalisch-Chemisches Institut der Universität, 355 Marburg, Biegenstrasse 12 (Germany)Physikalisch-Chemisches Institut der Universität, 355 Marburg, Biegenstrasse 12 (Germany)Search for more papers by this author Prof. Dr. Reinhard W. Hoffmann, Prof. Dr. Reinhard W. Hoffmann Fachbereich Chemie der Universität, 355 Marburg, Lahnberge (Germany)Search for more papers by this authorDipl.-Chem. Reinhard Schüttler, Dipl.-Chem. Reinhard Schüttler Fachbereich Chemie der Universität, 355 Marburg, Lahnberge (Germany)Search for more papers by this authorDipl.-Chem. Werner Schäfer, Dipl.-Chem. Werner Schäfer Physikalisch-Chemisches Institut der Universität, 355 Marburg, Biegenstrasse 12 (Germany)Search for more papers by this authorProf. Dr. Armin Schweig, Corresponding Author Prof. Dr. Armin Schweig Physikalisch-Chemisches Institut der Universität, 355 Marburg, Biegenstrasse 12 (Germany)Physikalisch-Chemisches Institut der Universität, 355 Marburg, Biegenstrasse 12 (Germany)Search for more papers by this author First published: June 1972 https://doi.org/10.1002/anie.197205121Citations: 27 † Theory and Application of Photoelectron Spectroscopy, Part 6.–Part 5: [14]. ‡ This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. The calculations were carried out by the Deutsches Rechenzentrum at Darmstadt. 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 Theory and Application of Photoelectron Spectroscopy, Part 6.–Part 5: [14]. 2 D. Lloyd: Carbocyclic Non-Benzenoid Aromatic Compounds. Elsevier, Amsterdam 1966, p. 153. 3 Prepared from quadricyclanone by a Wittig reaction in THF, giving 3-methylenetetracyclo[3.2.0.02, 7.04, 6]heptane (50%) [b.p. 143 °C; NMR (CCl4): τ = 4.95 (s), 8.17 (d), 8.52 ppm (t) as 2:4:2; IR: 3075, 1680, 1232, 748 cm−1], and rearrangement thereof to (1) by catalysis with norbornadiene-palladium chloride. After gas-chromatographic separation, yield 40%. [b.p. 119 °C; NMR (CCl4,): τ = 3.28 (t), 6.26 (p), 6.48 (s) as 4:2:2; UV (CH3OH): shoulder at 235 nm (ε=60); IR: 3070, 2995, 1685, 1665, 850, 730, 720, 623 cm−1;m/e = 104, 103, 78]. 4 M. J. Goldsrein and R. Hoffmann, J. Amer. Chem. Soc. 93, 6193 (1971). 5 E. Heilbronner and H. D. Martin, Helv. Chim. Acta, in press, discuss extensively this type of interaction for a derivative of (1), cf. H. D. Martin and B. Forster, Angew. Chem. 84, 65 (1972); Angew. Chem. internat. Edit. 11, 54 (1972). 6 P. Bischof, J. A. Hashmall, E. Heilbronner, and V. Hornung, Helv. Chim. Acta 52, 1745 (1969). 7 9-Methylenebicyclo[4.2.1]nona-2,4,7-triene should have the opposite polarization; this is under investigation. 8 Prepared from 7-norbornanone by a Wittig reaction in THF [b.p. 118.5°C; NMR (CCl4): τ = 5.55 (s), 7.75 (p), 8.55 ppm (m) as 2:2:8; IR: 1675, 885, 685 cm−1]. 9 K. Hatada, K. Nagata, and H. Yuki, Bull. Chem. Soc. Japan 43, 3195, 3267 (1970); cf. R. C. Haddon, V. R. Haddon, and L. M. Jackman, Fortschr. Chem. Forsch. 16, 103 (1971). 10 J. B. Grutzner, M. Jautelat, J. B. Dence, R. A. Smith, and J. D. Roberts, J. Amer. Chem. Soc. 92, 7107 (1970). 11 J. A. Pople and D. L. Beveridge: Approximate Molecular Orbital Theory. McGraw-Hill, New York 1970. 12 The Hel (584 Å) photoelectron spectra were determined with a PS 16 spectrometer from Perkin-Elmer Ltd., Beaconsfield (England). 13 M. J. S. Dewar: The Molecular Orbital Theory of Organic Chemistry. McGraw-Hill, New York 1969. 14 U. Weidner and A. Schweig, J. Organometal. Chem., in press. Citing Literature Volume11, Issue6June 1972Pages 512-513 ReferencesRelatedInformation
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