The Synthesis of Tetradehydrobenzocyclotetradecenes(“Benzodidehydro[14]annulenes”). The Effect of Benzoannelation on the Diamagnetic Ring Current of Macrocyclic (4 n + 2) π‐Electron Systems
1974; Wiley; Volume: 13; Issue: 2 Linguagem: Inglês
10.1002/anie.197401411
ISSN1521-3773
AutoresRex T. Weavers, Franz Sondheimer,
Tópico(s)Photochromic and Fluorescence Chemistry
ResumoAngewandte Chemie International Edition in EnglishVolume 13, Issue 2 p. 141-142 Communication The Synthesis of Tetradehydrobenzocyclotetradecenes(“Benzodidehydro[14]annulenes”). The Effect of Benzoannelation on the Diamagnetic Ring Current of Macrocyclic (4n + 2) π-Electron Systems†‡ Dr. Rex T. Weavers, Corresponding Author Dr. Rex T. Weavers Chemistry Department, University College, Gordon Street, London WC1H OAJ (England)Chemistry Department, University College, Gordon Street, London WC1H OAJ (England)Search for more papers by this authorProf. Dr. Franz Sondheimer, Prof. Dr. Franz Sondheimer Chemistry Department, University College, Gordon Street, London WC1H OAJ (England)Search for more papers by this author Dr. Rex T. Weavers, Corresponding Author Dr. Rex T. Weavers Chemistry Department, University College, Gordon Street, London WC1H OAJ (England)Chemistry Department, University College, Gordon Street, London WC1H OAJ (England)Search for more papers by this authorProf. Dr. Franz Sondheimer, Prof. Dr. Franz Sondheimer Chemistry Department, University College, Gordon Street, London WC1H OAJ (England)Search for more papers by this author First published: February 1974 https://doi.org/10.1002/anie.197401411Citations: 16 † Unsaturated macrocyclic compounds. Part 105.—Part 104: R. T. Weavers and F. Sondheimer, Angew. Chem. 86, 163 (1974); Angew. Chem. internat. Edit. 13, 138 (1974). ‡ We thank the Science Research Council for financial support. 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 1Unsaturated macrocyclic compounds. Part 105.—Part 104: R. T. Weavers and F. Sondheimer, Angew. Chem. 86, 163 (1974); Angew. Chem. internat. Edit. 13, 138 (1974). 2For references, see R. C. Haddon, V. R. Haddon, and L. M. Jackman, Fortsch. Chem. Forsch. 16, 103 (1971); F. Sondheimer, Accounts Chem. Res. 5, 81 (1972). 3See K. Endo, Y. Sakata, and S. Misumi, Tetrahedron Lett. 1970, 2557; H. Günther, H. Schmickler, H. Königshofen, K. Recker, and E. Vogel, Angew. Chem. 85, 261 (1973); Angew. Chem. internat. Edit. 12, 243 (1973). 4 C. E. Griffin, K. R. Martin, and B. E. Douglas, J. Org. Chem. 27, 1627 (1962); C. E. Griffin and J. A. Peters, J. Org. Chem. 28, 1715 (1963). 5 E. R. H. Jones and B. C. L. Weedon, J. Chem. Soc. 1946, 937; I. M. Heilbron, E. R. H. Jones, and M. Julia, J. Chem. Soc. 1949, 1430. 6 P. J. Beeby and F. Sondheimer, Angew. Chem. 85, 406 (1973); Angew. Chem. internat. Edit. 12, 411 (1973). 7 Substance (8) was followed by 6% of the corresponding di-cis isomer, yellow crystals which decomposed on attempted melting point determination [m/e 336.189 (calcd. 336.188); λmax (ether) 281 (ε 16900) and 356 nm sh (4400)]. The 1H-NMR spectrum of this isomer [CCl4, 100 MHz: τ = 2.88 (2H/m, benzenoid), 3.08 (2H/m, benzenoid), 3.68 (2H/d, J = 12.5 Hz, olefinic), 4.32 (2H/broad d, J = 12.5 Hz, olefinic), 7.65 (4H/m, allylic), 7.95 (4 H/m, allylic), and 8.3(8H/m, nonallylic)] showed it to be atropic, and it is presumably a nonplanar molecule. 8 The 1H-NMR spectrum of (4) was essentially temperature independent in the range −80 to 60°. 9See D. Cremer and H. Günther, Liebigs Ann. Chem. 763, 87 (1972). 10See, inter al., H. P. Figeys, Chem. Commun. 1967, 495; P. J. Garratt and K. P. C. Vollhardt, Angew. Chem. 83, 111 (1971); Angew. Chem. internat. Edit. 10, 125 (1971); P. J. Garratt and K. P. C. Vollhardt, J. Amer. Chem. Soc. 94, 7087 (1972). 11 P. J. Beeby, R. T. Weavers, and F. Sondheimer, Angew. Chem. 86, 165 (1974); Angew. Chem. internat. Edit. 13, 139 (1974). Citing Literature Volume13, Issue2February 1974Pages 141-142 ReferencesRelatedInformation
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