Syntheses of syn and anti doublebent [5]phenylene

Organic Letters

Volumn 6, Issue 13, 2004, Pages 2249-2252

  Bong, Dennis T Y ^f   Chan, Eugene W L ^f   Diercks, Rainer ^f   Dosa, Peter I ^f   Haley, Michael M ^f   Matzger, Adam J ^f   Miljanić, Ognjen Š ^f   Vollhardt, K Peter C ^f   Bond, Andrew D ^a,e   Teat, Simon J ^b   Stanger, Amnon ^c,d  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b DARESBURY LABORATORY   (United Kingdom)

^c Department of Chemistry   (Israel)

^d TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^e UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^f NONE

Author keywords

[No Author keywords available]

Indexed keywords

PHENAZONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR INTERACTION; MOLECULAR MECHANICS; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; X RAY ANALYSIS;

EID: 3142721246     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049225v     Document Type: Article

References (23)

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2. For a review, see: (a) Vollhardt, K. P. C.; Mohler, D. L. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI: London, 1996; pp 121-160. For recent progress, see: (b) Han, S.; Bond, A. D.; Disch, R. L.; Holmes, D.; Schulman, J. M.; Teat, S. J.; Vollhardt, K. P. C.; Whitener, G. D. Angew. Chem., Int. Ed. 2002, 41, 3223. (c) Han, S.; Anderson, D. R.; Bond, A. D.; Chu, H. V.; Disch, R. L.; Holmes, D.; Schulman, J. M.; Teat, S. J.; Vollhardt, K. P. C.; Whitener, G. D. Angew. Chem., Int. Ed. 2002, 41, 3227. (d) Bruns, D.; Miura, H.; Vollhardt, K. P. C.; Stanger, A. Org. Lett. 2003, 5, 549.
3. For a review, see: (a) Vollhardt, K. P. C.; Mohler, D. L. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI: London, 1996; pp 121-160. For recent progress, see: (b) Han, S.; Bond, A. D.; Disch, R. L.; Holmes, D.; Schulman, J. M.; Teat, S. J.; Vollhardt, K. P. C.; Whitener, G. D. Angew. Chem., Int. Ed. 2002, 41, 3223. (c) Han, S.; Anderson, D. R.; Bond, A. D.; Chu, H. V.; Disch, R. L.; Holmes, D.; Schulman, J. M.; Teat, S. J.; Vollhardt, K. P. C.; Whitener, G. D. Angew. Chem., Int. Ed. 2002, 41, 3227. (d) Bruns, D.; Miura, H.; Vollhardt, K. P. C.; Stanger, A. Org. Lett. 2003, 5, 549.
4. For a review, see: (a) Vollhardt, K. P. C.; Mohler, D. L. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI: London, 1996; pp 121-160. For recent progress, see: (b) Han, S.; Bond, A. D.; Disch, R. L.; Holmes, D.; Schulman, J. M.; Teat, S. J.; Vollhardt, K. P. C.; Whitener, G. D. Angew. Chem., Int. Ed. 2002, 41, 3223. (c) Han, S.; Anderson, D. R.; Bond, A. D.; Chu, H. V.; Disch, R. L.; Holmes, D.; Schulman, J. M.; Teat, S. J.; Vollhardt, K. P. C.; Whitener, G. D. Angew. Chem., Int. Ed. 2002, 41, 3227. (d) Bruns, D.; Miura, H.; Vollhardt, K. P. C.; Stanger, A. Org. Lett. 2003, 5, 549.
5. For an exposé of the significance of this class of molecules in graph theoretical treatments of aromaticity, see: (a) Randić, M. Chem. Rev. 2003, 103, 3449. For selected other studies, see: (b) Schulman, J. M.; Disch, R. L. J. Phys. Chem. A. 2003, 107, 5223. (c) Schulman, J. M.; Disch, R. L.; Jiao, H.; Schleyer, P. v. R. J. Phys. Chem. A 1998, 102, 8051. (d) Schulman, J. M.; Disch, R. L. J. Phys. Chem. A 1997, 101, 5596. The calculations reported in this paper were repeated at the B3LYP/6-31G* level of DFT theory in the present work; NICS (1.0) at GIAO/3-21G. See Supporting Information.
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7. For an exposé of the significance of this class of molecules in graph theoretical treatments of aromaticity, see: (a) Randić, M. Chem. Rev. 2003, 103, 3449. For selected other studies, see: (b) Schulman, J. M.; Disch, R. L. J. Phys. Chem. A. 2003, 107, 5223. (c) Schulman, J. M.; Disch, R. L.; Jiao, H.; Schleyer, P. v. R. J. Phys. Chem. A 1998, 102, 8051. (d) Schulman, J. M.; Disch, R. L. J. Phys. Chem. A 1997, 101, 5596. The calculations reported in this paper were repeated at the B3LYP/6-31G* level of DFT theory in the present work; NICS (1.0) at GIAO/3-21G. See Supporting Information.
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20. Assignments were made on the basis of signal multiplicity, including the simplification of the spectra in 1b and 2b, comparison to the NMR spectra of 3-5, and calculated chemical shifts (see Supporting Information).
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22. As defined in: Beckhaus, H.-D.; Faust, R.; Matzger, A. J.; Mohler, D. L.; Rogers, D. W.; Rüchardt, C.; Sawhney, A. K.; Verevkin, S. P.; Vollhardt, K. P. C.; Wolff, S. J. Am. Chem. Soc. 2000, 122, 7819.
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