Conformational and Electronic Engineering of Twisted Diphenylacetylenes

Organic Letters

Volumn 5, Issue 21, 2003, Pages 3951-3954

  Brizius, Glen ^a,b   Billingsley, Kelvin ^b   Smith, Mark D ^b   Bunz, Uwe H F ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALKYNE; BENZENE; CARBON;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ENGINEERING; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONFORMATION; ELECTRONICS; FLUORESCENCE; QUANTUM CHEMISTRY; RING CLOSING METATHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0242628398     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035532+     Document Type: Article

References (29)

1. McFarland, S. A.; Finney, N. S. J. Am. Chem. Soc. 2002, 124, 1178-1179.
2. (a) Bunz, U. H. F. Acc. Chem. Res. 2001, 34, 998-1010.
3. (b) Sluch, M. I.; Godt, A.; Bunz, U. H. F.; Berg, M. A. J. Am. Chem. Soc. 2001, 123, 6447-6448.
4. (c) Levitus, M.; Schmieder, K.; Ricks, H.; Shimizu, K. D.; Bunz, U. H. F.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2001, 123, 4259-4265.
5. (d) Miteva, T.; Palmer, L.; Kloppenburg, L.; Neher, D.; Bunz, U. H. F. Macromolecules 2000, 33, 652-654.
6. (e) Halkyard, C. E.; Rampey, M. E.; Kloppenburg, L.; Studer-Martinez, S. L.; Bunz, U. H. F. Macromolecules 1998, 31, 8655-8659.
7. (a) Kim, J.; Levitsky, I. A.; McQuade, D. T.; Swager, T. M. J. Am. Chem. Soc. 2002, 124, 7710-7718.
8. (b) Kim, J.; Swager, T. M. Nature 2001, 411, 1030-1034; Nature 2001, 413, 548 (correction)
9. (b) Kim, J.; Swager, T. M. Nature 2001, 411, 1030-1034; Nature 2001, 413, 548 (correction)
10. (c) Zhou, Q.; Swager, T. M. J. Am. Chem. Soc. 1995, 117, 12593-12603.
11. Beeby, A.; Findlay, K.; Low, P. J.; Marder, T. B. J. Am. Chem. Soc. 2002, 124, 8280-8284.
12. The rotational barrier of tolane is calculated to 0.86 kcal/mol utilizing a B3PW91/6-311G** basis set: Seminario, J. M.; Zacarias, A. G.; Tour, J. M. J. Am. Chem. Soc. 1998, 120, 3970-3974.
13. Moore, J. S. Acc. Chem. Res. 1997, 30, 402-413. Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793-1796.
14. Moore, J. S. Acc. Chem. Res. 1997, 30, 402-413. Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793-1796.
15. (a) Crisp, G. T.; Bubner, T. P. Tetrahedron 1997, 53, 11881-11898.
16. (b) Crisp, G. T.; Bubner, T. P. Tetrahedron 1997, 53, 11899-11912.
17. Bunz, U. H. F. Chem Rev. 2000, 100, 1605-1644. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49.
18. Bunz, U. H. F. Chem Rev. 2000, 100, 1605-1644. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49.
19. Grela, K.; Ignatowska, J. Org. Lett. 2002, 4, 3747-3749.
20. (a) Brizius, G.; Bunz, U. H. F. Org. Lett. 2002, 4, 2829-2831.
21. (b) Kloppenburg, L.; Song, D.; Bunz, U. H. F. J. Am. Chem. Soc. 1998, 120, 7973-7974.
22. Mortreux, A.; Blanchard, M. J. Chem. Soc., Chem. Commun. 1974, 786-787.
23. (b) Kaneta, N.; Hikichi, K.; Mori, M. Chem. Lett. 1995, 1055-1066.
24. (c) Kaneta, N.; Hirai, T.; Mori, M. Chem. Lett. 1995, 627-628.
25. (a) Weck, M.; Dunn, A. R.; Matsumoto, K.; Coates, G. W.; Lobkovsky E. B. ; Grubbs, R. H. Angew. Chem., Int. Ed. 1999, 38, 2741-2744.
26. (b) Coates, G. W.; Dunn, A. R.; Henling, L. M.; Dougherty, D. A.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 248-251.
27. Bunz, U. H. F.; Enkelmann, V. Chem. Eur. J. 1999, 5, 263-266.
28. (a) Dai, C.; Nguyen, P.; Marder T. B.; Scott, A. J.; Clegg, W.; Viney, C. Chem. Commun. 1999, 2493-2494.
29. (b) Collings, J. C.; Roscoe, K. P.; Robins, E. G.; Batsanov, A. S.; Stimson, L. N.; Howard, J. A. K.; Clark, S. J.; Marder, T. B. New J. Chem. 2002, 26, 1740-1746.