We present herein an overview of our ongoing studies with dendralenes. The first synthetic routes to this fundamental family of compounds have revealed long-hidden secrets in hydrocarbon chemistry and set the scene for synthetic and materials chemistry applications.
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Pure and Applied Chemistry
The Scientific Journal of IUPAC
Ed. by Burrows, Hugh / Stohner, Jürgen
IMPACT FACTOR 2017: 5.294
CiteScore 2017: 3.42
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- Online
- ISSN
- 1365-3075
Demystifying the dendralenes
Emily G. Mackay / Michael S. Sherburn
Published Online: 2013-05-15 | DOI: https://doi.org/10.1351/PAC-CON-13-02-04
Free Access
Keywords: cycloadditions; dendralenes; domino reactions; hydrocarbons; organic synthesis; polycyclic compounds; polyenes
Conference
International Conference on Organic Synthesis (ICOS-19), International Conference on Organic Synthesis, ICOS, Organic Synthesis, 19th, Melbourne, Australia, 2012-07-01–2012-07-06
References
- 1
, H. Hopf. Angew. Chem., Int. Ed. Engl.23, 948 (1984).CrossrefGoogle Scholar
- 2
For reviews on the linear polyenes, see.Google Scholar
- 2a
, B. Hudson, B. Kohler. Ann. Rev. Phys. Chem.25, 437 (1974).CrossrefGoogle Scholar
- 2b
B. S. Hudson, B. E. Kohler, K. Schulten. In Excited States, Vol. 6, E. C. Lim (Ed.), pp. 1–95, Academic Press, New York (1982).Google Scholar
- 2c
, B. Hudson, B. Kohler. Synth. Met.9, 241 (1984).CrossrefGoogle Scholar
- 2d
, B. E. Kohler. J. Chem. Phys.93, 5838 (1990); for reviews on the annulenes, see.CrossrefGoogle Scholar
- 2e
F. Sondheimer, I. C. Calder, J. A. Elix, Y. Gaoni, P. J. Garratt, K. Grohmann, G. Di Maio, J. Mayer, M. V. Sargent, R. Wolovsky. Chem. Soc. Spec. Publ. No. 21, 75 (1967).Google Scholar
- 2f
, F. Sondheimer. Pure Appl. Chem.28, 331 (1971).CrossrefGoogle Scholar
- 2g
P. J. Garrat. In Comprehensive Organic Chemistry, Vol. 1, D. H. R. Barton, W. D. Ollis (Eds.), p. 361, Pergamon Press, Oxford (1979).Google Scholar
- 2h
, E. L. Spitler, C. A. Johnson, M. M. Haley. Chem. Rev.106, 5344 (2006).CrossrefGoogle Scholar
- 3
For reviews on the radialenes, see.Google Scholar
- 3a
, H. Hopf, G. Maas. Angew. Chem., Int. Ed. Engl.31, 931 (1992).CrossrefGoogle Scholar
- 3b
G. Maas, H. Hopf. In The Chemistry of Dienes and Polyenes, Vol. 1, Z. Rappoport (Ed.), pp. 927–977, John Wiley, Chichester (1997).Google Scholar
- 3c
, R. R. Tykwinski, M. Gholami, S. Eisler, Y. Zhao, F. Melin, L. Echegoyen. Pure Appl. Chem.80, 621 (2008);CrossrefGoogle Scholar
- 3d
, for a review on the fulvenes, see: A. P. Scott, I. Agranat, P. U. Biedermann, N. V. Riggs, L. Radom. J. Org. Chem.62, 2026 (1997).CrossrefGoogle Scholar
- 4
S. Fielder, D. D. Rowan, M. S. Sherburn. Angew. Chem., Int. Ed.39, 4331 (2000).Google Scholar
- 5
, H. Hopf, M. S. Sherburn. Angew. Chem., Int. Ed.51, 2298 (2012).CrossrefGoogle Scholar
- 6a
, A. T. Blomquist, J. A. Verdol. J. Am. Chem. Soc.77, 81 (1955).CrossrefGoogle Scholar
- 6b
, W. J. Bailey, J. Economy. J. Am. Chem. Soc.77, 1133 (1955).CrossrefGoogle Scholar
- 6c
, W. J. Bailey, C. H. Cunov, L. Nicholas. J. Am. Chem. Soc.77, 2787 (1955).CrossrefGoogle Scholar
- 7
, W. S. Trahanovsky, K. A. Koeplinger. J. Org. Chem.57, 4711 (1992).CrossrefGoogle Scholar
- 8
, J. I. G. Cadogan, S. Cradock, S. Gillam, I. Gosney. J. Chem. Soc., Chem. Commun. 114 (1991).CrossrefGoogle Scholar
- 9a
, S. P. Bew, J. B. Sweeney. Synthesis 698 (1994).CrossrefGoogle Scholar
- 9b
, S. P. Bew, J. B. Sweeney. Synlett 1273 (1997).CrossrefGoogle Scholar
- 10
, H. Hopf. Angew. Chem., Int. Ed.40, 705 (2001).CrossrefGoogle Scholar
- 11
, A. D. Payne, A. C. Willis, M. S. Sherburn. J. Am. Chem. Soc.127, 12188 (2005).CrossrefGoogle Scholar
- 12
, A. D. Payne, G. Bojase, M. N. Paddon-Row, M. S. Sherburn. Angew. Chem., Int. Ed.48, 4836 (2009).CrossrefGoogle Scholar
- 13
, T. A. Bradford, A. D. Payne, A. C. Willis, M. N. Paddon-Row, M. S. Sherburn. J. Org. Chem.75, 491 (2010).CrossrefGoogle Scholar
- 14
, F. Sondheimer, D. A. Ben-Efraim, R. Wolovsky. J. Am. Chem. Soc.83, 1675 (1961).CrossrefGoogle Scholar
- 15
, M. N. Paddon-Row, M. S. Sherburn. Chem. Commun.48, 832 (2012).CrossrefGoogle Scholar
- 16
Notable recent examples include.Google Scholar
- 16a
, S. Kanemasa, H. Sakoh, E. Wada, O. Tsuge. Bull. Chem. Soc. Jpn.59, 1869 (1986).CrossrefGoogle Scholar
- 16b
, K. M. Brummond, H. Chen, P. Sill, L. You. J. Am. Chem. Soc.124, 15186 (2002).CrossrefGoogle Scholar
- 16c
, M. S. Souweha, A. Arab, M. ApSimon, A. G. Fallis. Org. Lett.9, 615 (2007).CrossrefGoogle Scholar
- 16d
, J. Le Paih, C. V.-L. Bray, S. Dérien, P. H. Dixneuf. J. Am. Chem. Soc.132, 7391 (2010).CrossrefGoogle Scholar
- 17a
, T. A. Bradford, A. D. Payne, A. C. Willis, M. N. Paddon-Row, M. S. Sherburn. Org. Lett.9, 4861 (2007).CrossrefGoogle Scholar
- 17b
, N. A. Miller, A. C. Willis, M. N. Paddon-Row, M. S. Sherburn. Angew. Chem., Int. Ed.46, 937 (2007).CrossrefGoogle Scholar
- 17c
, H. Toombs-Ruane, E. L. Pearson, M. N. Paddon-Row, M. S. Sherburn. Chem. Commun.48, 6639 (2012).CrossrefGoogle Scholar
- 18
, X. Zeng, Q. Hu, M. Qian, E.-i. Negishi. J. Am. Chem. Soc.125, 13636 (2003).CrossrefGoogle Scholar
- 19
, H. Toombs-Ruane, N. Osinski, T. Fallon, C. Wills, A. C. Willis, M. N. Paddon-Row, M. S. Sherburn. Chem. Asian J.6, 3243 (2011).CrossrefGoogle Scholar
- 20
, G. Bojase, T. V. Nguyen, A. D. Payne, A. C. Willis, M. S. Sherburn. Chem. Sci.2, 229 (2011).CrossrefGoogle Scholar
- 21
, Z. Yang, J. C. Lorenz, Y. Shi. Tetrahedron Lett.39, 8621 (1998).CrossrefGoogle Scholar
- 22
, O. Tsuge, E. Wada, S. Kanemasa. Chem. Lett.12, 239 (1983).CrossrefGoogle Scholar
- 23
R. Paul, S. Tchelitcheff. C. R. Hebd. Seances Acad. Sci.232, 1939 (1951).Google Scholar
- 24
, G. Bojase, A. D. Payne, A. C. Willis, M. S. Sherburn. Angew. Chem., Int. Ed.47, 910 (2008).CrossrefGoogle Scholar
- 25
, N. A. Miller, A. C. Willis, M. S. Sherburn. Chem. Commun. 1226 (2008).CrossrefGoogle Scholar
- 26
, C. K. Lai, R. S. Buckanin, S. J. Chen, D. F. Zimmerman, F. T. Sher, G. A. Berchtold. J. Org. Chem.47, 2364 (1982).CrossrefGoogle Scholar
- 27
, S. V. Pronin, R. A. Shenvi. J. Am. Chem. Soc.134, 19604 (2012).CrossrefGoogle Scholar
- 28a
, A. Vasella. Helv. Chim. Acta60, 1273 (1977).CrossrefGoogle Scholar
- 28b
, B. M. Aebischer, H. W. Hanssen, A. T. Vasella, W. B. Schweizer. J. Chem. Soc., Perkin Trans. 1 2139 (1982).CrossrefGoogle Scholar
- 28c
, H. Felber, G. Kresze, R. Prewo, A. Vasella. Helv. Chim. Acta69, 1137 (1986).CrossrefGoogle Scholar
- 28d
, A. Basha, R. Henry, M. A. McLaughlin, J. D. Ratajczyk, S. J. Wittenberger. J. Org. Chem.59, 6103 (1994).CrossrefGoogle Scholar
- 29
, R. Wang, G. Bojase, A. C. Willis, M. N. Paddon-Row, M. S. Sherburn. Org. Lett.14, 5652 (2012).CrossrefGoogle Scholar
- 30
, K. M. Cergol, C. G. Newton, A. L. Lawrence, A. C. Willis, M. N. Paddon-Row, M. S. Sherburn. Angew. Chem., Int. Ed.50, 10425 (2011).CrossrefGoogle Scholar
About the article
Published Online: 2013-05-15
Published in Print: 2013-05-15
Citation Information: Pure and Applied Chemistry, Volume 85, Issue 6, Pages 1227–1239, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-13-02-04.
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