Are terminal aryl butadiynes stable? Synthesis and X-ray crystal structures of a series of aryl- and heteroaryl-butadiynes (Ar-C≡C-C≡C-H)

Journal of Organic Chemistry

Volumn 71, Issue 22, 2006, Pages 8541-8544

  West, Kara ^a   Wang, Changsheng ^a   Batsanov, Andrei S ^a   Bryce, Martin R ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CONCENTRATION (PROCESS); CRYSTAL STRUCTURE; DERIVATIVES; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

DILUTE SOLUTIONS; X-RAY CRYSTAL STRUCTURES;

HYDROCARBONS;

1,3 BUTADIENE; 2 METHYL 6 (2 PYRAZYL)HEXA 3,5 DIYN 2 OL; 2 METHYL 6 (2 PYRIDYL)HEXA 3,5 DIYN 2 OL; 2 METHYL 6 (4 BIPHENYL)HEXA 3,5 DIYN 2 OL; 2 METHYL 6 (4 PYRIDYL)HEXA 3,5 DIYN 2 OL; 2 METHYL 6 [2 (9 FLUORENONYL)]HEXA 3,5 DIYN 2 OL; AROMATIC HYDROCARBON; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CONCENTRATION (PARAMETERS); CRYSTAL STRUCTURE; DILUTION; ISOLATION AND PURIFICATION; NONHUMAN; SOLUTION AND SOLUBILITY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 33750476684     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0615697     Document Type: Article

References (41)

1. Acetylene Chemistry: Chemistry, Biology and Material Science; Diederich, F., Stang, P. J., Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
2. Carbon-Rich Compounds: From Molecules to Materials; Haley, M. M., Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, Germany, 2006.
3. (a) Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Chem. Soc. Rev. 1999, 28, 107-119.
4. (b) Nielsen, M. B.; Diederich, F. Chem. Rev. 2005, 105, 1837-1867.
5. (c) Marsden, J. A.; Miller, J. J.; Shirtcliffe, L. D.; Haley, M. M. J. Am. Chem. Soc. 2005, 127, 2464-2476.
6. (d) Bowling, N. P.; Halter, R. J.; Hodges, J. A.; Seburg, R. A.; Thomas, P. S.; Simmons, C. S.; Stanton, J. F.; McMahon, R. J. J. Am. Chem. Soc. 2006, 128, 3291-3302.
7. Cornil, J.; Beljonne, D.; Calbert, J.-P.; Brédas, J.-L. Adv. Mater. 2001, 13, 1053-1119
8. (a) Rogers, D. W.; Matsunaga, N.; Zavitsas, A. A.; McLafferty, F. J.; Liebman, J. F. Org. Lett. 2003, 5, 2373-2375.
9. (b) Jarowski, P. D.; Wodrich, M. D.; Wannere, C. S.; Schleyer, P. v. R.; Houk, K. N. J. Am. Chem. Soc. 2004, 126, 15036-10537.
10. Mohr, W.; Stahl, J.; Hampel, F.; Gladysz, J. A. Chem.-Eur. J. 2003, 9, 3324-3340.
11. (a) Eisler, S.; Chahal, N.; McDonald, R.; Tykwinski, R. R. Chem.-Eur. J. 2003, 9, 2542-2550.
12. (b) Eisler, S.; Slepkov, A. D.; Elliott, E.; Luu, T.; McDonald, R.; Hegmann, F. A.; Tykwinski, R. R. J. Am. Chem. Soc. 2005, 127, 2666-2676.
13. (a) Eastmond, R.; Walton, D. R. M. Tetrahedron 1972, 28, 4591-4599.
14. (b) Ziessel, R.; Suffert, J. Tetrahedron Lett. 1996, 12, 2011-2014.
15. (c) Heuft, M. A.; Collins, S. K.; Yap, G. P. A.; Fallis, A. G. Org. Lett. 2001, 3, 2883-2886.
16. (d) Zhou, N.; Merschrod, S. E. F.; Zhao, Y. J. Am. Chem. Soc. 2005, 127, 14154-14155.
17. (a) Kende, A. S.; Smith, C. A. J. Org. Chem. 1988, 53, 2655-2657.
18. (b) Liu, L.; Wong, W.-Y.; Poon, S.-Y.; Shi, J.-X.; Cheah, K.-W.; Lin, Z. Chem. Mater. 2006, 18, 1369-1378.
19. (c) Lewis, J.; Khan, M. S.; Kakkar, A. K.; Johnson, B. F. G.; Marder, T. B.; Fyfe, H. B.; Wittmann, F.; Friend, R. H.; Dray, A. E. J. Organomet. Chem. 1992, 425, 165-176.
20. Karatholuvhu, M. S.; Fuchs, P. L. J. Am. Chem. Soc. 2004, 126, 14314-14315.
21. For statements on the instability of simple ArC≡CC≡CH species, see: (a) Morisaki, Y.; Luu, T.; Tykwinski, R. R. Org. Lett. 2006, 8, 689-692. This paper states that "aryl butadiynes are unstable to isolation."
22. (b) Heuft, M. A.; Collins, S. K.; Yap, G. P. A.; Fallis, A. G. Org. Lett. 2001, 3, 2883-2886.
23. (c) Haley, M. M.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakely, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956-2957.
24. (d) Graham, E. M.; Miskowski, V. M.; Perry, J. W.; Coulter, D. R.; Stiegman, A. E.; Schaefer, W. P.; Marsh, R. E. J. Am. Chem. Soc. 1989, 111, 8771-8779.
25. (e) Yuan, Z.; Stringer, G.; Jobe, I. R.; Kreller, D.; Scott, K.; Koch, L.; Taylor, N. J.; Marder, T. B. J. Organomet. Chem. 1993, 452, 115-120.
26. (f) Wan, W. B.; Haley, M. M. J. Org. Chem. 2001, 66, 3893-3901 and references therein.
27. (g) Brandsma, L. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 2004; p 360 describes PhC≡CC≡CH as "extremely unstable".
28. Nielsen, M. B.; Utesch, N. F.; Moonen, N. N. P.; Boudon, C.; Gisselbrecht, J.-P.; Concilio, S.; Piotto, S. P.; Seiler, P.; Günter, P.; Gross, M.; Diederich, F. Chem.-Eur. J. 2002, 8, 3601-3613.
29. Wang, C.; Pålsson, L.-O.; Batsanov, A. S.; Bryce, M. R. J. Am. Chem. Soc. 2006, 128, 3789-3799.
30. Dabdoub, M. J.; Baroni, A. C. M.; Lenardão, E. J.; Gianeti, T. R.; Hurtado, G. R. Tetrahedron Lett. 2001, 57, 4271-4276.
31. Gusev, I.; Kucherov, V. F. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1962, 995-999.
32. Marsden, J. A.; Haley, M. M. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 1, Chapter 6.
33. (l7) The acetone protecting group has been used for the synthesis of alkylbutadiynes: (a) Carpita, A.; Neri, D.; Rossi, R. Gazz. Chim. Ital. 1987, 117, 481-489.
34. (b) Dabdoub, M. J.; Dabdoub, V. B.; Lenardão, E. J. Tetrahedron Lett. 2001, 42, 1807-1809.
35. Malone, J. F.; Murray, C. M.; Charlton, M. H.; Docherty, R.; Lavery, A. J. J. Chem. Soc., Faraday Trans. 1997, 93, 3429-3436.
36. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press: Oxford, 1999.
37. (a) Baughman, R. H. J. Appl. Phys. 1972, 43, 4362-4370.
38. (b) Enkelmann, V. Chem. Mater. 1994, 6, 1337-1340.
39. (c) Coates, G. W.; Dunn, A. R.; Henling, L. M.; Dougherty, D. A.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 248-251.
40. Enkelmann, V. Adv. Polym. Sci. 1984, 63, 91-136.
41. Armitage, J. B.; Entwistle, N.; Jones, E. R. H.; Whiting, M. C. J. Chem. Soc. 1954, 147-154.