Synthesis of oligo(1,6-heptadiynes) with a single structure and terminal methylene groups using molybdenum-based wittig and metathesis chemistry. 1. 2,6-dimethylphenylimido systems

Organometallics

Volumn 27, Issue 23, 2008, Pages 6202-6214

  Scriban, Corina ^a   Schrock, Richard R ^a   Müller, Peter ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPOLYMERIZATION; DOUBLE BONDS; HIGH YIELDS; HOMOCHIRAL; METATHESIS CHEMISTRIES; METATHESIS REACTIONS; METHYLENE GROUPS; OLIGOENES; PENTAMER; QUINUCLIDINE; SINGLE STRUCTURES; SYNTHESIS OF; WITTIG REACTIONS; X-RAY STRUCTURES;

ALDEHYDES; CHEMICAL BONDS; CHEMICAL REACTIONS; FUNCTIONAL GROUPS; OPERATING ROOMS; ORGANIC COMPOUNDS;

MOLYBDENUM;

EID: 57849110573     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om8007585     Document Type: Article

References (38)

1. (a) Samuel, I. D. W. Philos. Trans. R. Soc. London, Ser. A 2000, 358, 193.
2. (b) Friend, R. H.; Gymer, R. W.; Holmes, A. B.; Burroughes, J. H.; Marks, R. N.; Taliani, C.; Bradley, D. D. C.; Dos Santos, D. A.; Bredas, J. L.; Logdlund, M.; Salaneck, W. R. Nature (London) 1999, 397, 121.
3. (a) Masuda, T.; Abdul Karim, S. M.; Nomura, R. J. Mol. Catal. A 2000, 160, 125.
4. (b) Masuda, T.; Higashimura, T. Adv. Polym. Sci. 1986, 81, 122.
5. (c) Mizumoto, T.; Masuda, T.; Higashimura, T. J. Polym. Sci. A: Polym Chem. 1993, 31, 2555.
6. (d) Masuda, T.; Higashimura, T. Acc. Chem. Res. 1984, 17, 51.
7. (e) Masuda, T.; Fujimori, J. I.; Abrahman, M. Z.; Higashimura, T. Polym. J. 1993, 25, 535.
8. (f) Masuda, T. J. Poly. Sci. A: Polym. Chem. 2007, 45, 165.
9. (a) Choi, S.-K.; Gal, Y.-S.; Jin, S.-H.; Kim, H. K. Chem. Rev. 2000, 100, 1645.
10. (b) Lam, J. W. Y.; Tang, B. Z. J. Polym. Sci. 2003, 41, 2607.
11. (c) Buchmeiser, M. R. Monatsh. Chem. 2003, 134, 327.
12. (d) Buchmeiser, M. R. Adv. Polym. Sci. 2005, 176, 89.
13. Martin, R. E.; Diedrich, F. Angew. Chem., Int. Ed. 1999, 38, 1350.
14. (a) Fox, H. H.; Schrock, R. R. Organometallics 1992, 11, 2763.
15. (b) Fox, H. H.; Wolf, M. O.; O'Dell, R.; Lin, B. L.; Schrock, R. R.; Wrighton, M. S. J. Am. Chem. Soc. 1994, 116, 2827.
16. (a) Schattenmann, F. J.; Schrock, R. R.; Davis, W. M. J. Am. Chem. Soc. 1996, 118, 3295.
17. (b) Schrock, R. R.; Tonzetich, Z. J.; Lichtscheidl, A. G.; Müller, P. Organometallics 2008, 27, 3986.
18. (a) Anders, U.; Nuyken, O.; Buchmeiser, M. R.; Wurst, K. Angew. Chem., Int. Ed. 2002, 41, 4044.
19. (b) Anders, U.; Nuyken, O.; Buchmeiser, M. R.; Wurst, K. Macromolecules 2002, 35, 9029.
20. (c) Anders, U.; Nuyken, O.; Buchmeiser, M. R. J. Mol. Catal. A 2004, 213, 89.
21. (a) Krause, J. O.; Zarka, M. T.; Anders, U.; Weberskirch, R.; Nuyken, O.; Buchmeiser, M. R. Angew. Chem. 2003, 115, 6147.
22. (b) Krause, J. O.; Nuyken, O.; Buchmeiser, M. R. Chem.-Eur. J. 2004, 10, 2029.
23. (c) Krause, J. O.; Wang, D.; Anders, U.; Weberskirch, R.; Zarka, M. T.; Nuyken, O.; Jäger; C.; Haarer, D.; Buchmeiser, M. R. Macromol. Symp. 2004, 217, 179.
24. (d) Halbach, T. S.; Krause, J. O.; Nuyken, O.; Buchmeiser, M. R. Macromol. Rapid Commun. 2005, 26, 784.
25. (e) Vygodskii, Y. S.; Shaplov, A. S.; Lozinskaya, E. I.; Vlasov, P. S.; Malyshkina, I. A.; Gavrilova, N. D.; Kumar, P. S.; Buchmeiser, M. R. Macromolecules 2008, 41, 1919.
26. (f) Mayershofer, M.; Nuyken, O.; Buchmeiser, M. R. Macromolecules 2006, 39, 3484.
27. Adamchuk, J.; Schrock, R. R.; Tonzetich, Z. J.; Müller, P. Organometallics 2006, 25, 2364.
28. Czekelius, C.; Hafer, J.; Tonzetich, Z. J.; Schrock, R. R.; Christensen, R. L.; Müller, P. J. Am. Chem. Soc. 2006, 128, 16664.
29. Crystallographic details can be found in tables submitted along with CIF files as part of the Supporting Information.
30. Experimental details can be found in the Supporting Information.
31. Schrock, R. R.; Gabert, A. J.; Singh, R.; Hock, A. S. Organometallics 2005, 24, 5058.
32. Yuan, P.; Wu, X.; Yu, G.; Du, D.; Liu, S. H. J. Organomet. Chem. 2007, 692, 3588.
33. Gabert, A. J.; Schrock, R. R.; Müller, P. Chem. Asian J. 2008, 5, 1535.
34. Schrock, R. R.; Crowe, W. E.; Bazan, G. C.; DiMare, M.; O'Regan, M. B.; Schofield, M. H. Organometallics 1991, 10, 1832.
35. Oskam, J. H.; Fox, H. H.; Yap, K. B.; McConville, D. H.; O'Dell, R.; Lichtenstein, B. J.; Schrock, R. R. J. Organomet. Chem. 1993, 459, 185.
36. (a) Trost, B. M.; Older, C. M. Organometallics 2002, 21, 2544.
37. (b) Kundig, E. P.; Monnier, F. R. Adv. Synth. Catal. 2004, 346, 901.
38. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122.