Insertion of carboryne into aromatic rings: Formation of cyclooctatetraenocarboranes

Journal of the American Chemical Society

Volumn 132, Issue 29, 2010, Pages 9988-9989

  Wang, Sunewang R ^a   Qiu, Zaozao ^a   Xie, Zuowei ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

[2 + 2] CYCLOADDITION; [4 + 2] CYCLOADDITION; AROMATIC RINGS; DEAROMATIZATION; SIGMATROPIC REARRANGEMENTS;

AROMATIC COMPOUNDS;

AROMATIZATION;

AROMATIC COMPOUND; CARBORANE DERIVATIVE; CYCLOOCTANE DERIVATIVE; CYCLOOCTATETRAENOCARBORANE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; REACTION ANALYSIS; SYNTHESIS; THERMAL ANALYSIS;

EID: 77955839365     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1044488     Document Type: Article

References (32)

1. (a) Mander, L. N. Synlett 1991, 134-144.
2. (b) Bach, T. Angew. Chem., Int. Ed. 1996, 35, 729-730.
3. For reviews, see: (a) Pape, A. R.; Kaliappan, K. P.; Kündig, P. Chem. Rev. 2000, 100, 2917-2940.
4. (b) Subba Rao, G. S. R. Pure Appl. Chem. 2003, 75, 1443-1451.
5. (c) Quideau, S.; Pouységu, L.; Deffieux, D. Synlett 2008, 467-495.
6. (a) Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic: New York, 1967.
7. (b) Kirmse, W. Carbene Chemistry, 2nd ed.; Academic: New York, 1971; Vol. 1.
8. (c) Cornelisse, J. Chem. Rev. 1993, 93, 615-669.
9. (d) Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701-730.
10. For recent examples, see: (a) Vo, N. T.; Pace, R. D. M.; O'Hara, F.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 404-405.
11. (b) Dong, S.; Zhu, J.; Porco, J. A., Jr. J. Am. Chem. Soc. 2008, 130, 2738-2739.
12. (c) García-Fortanet, J.; Kessler, F.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 6676-6677.
13. (d) Penkett, C. S.; Woolford, J. A.; Day, I. J.; Coles, M. P. J. Am. Chem. Soc. 2010, 132, 4-5.
14. Suzuki, H.; Tokitoh, N.; Okazaki, R. J. Am. Chem. Soc. 1994, 116, 11572-11573.
15. Gingrich, H. L.; Ghosh, T.; Huang, Q.; Jones, M., Jr. J. Am. Chem. Soc. 1990, 112, 4082-4083.
16. (a) Atkins, J. H.; Ho, D. M.; Jones, M., Jr. Tetrahedron Lett. 1996, 37, 7217-7220.
17. (b) Ghosh, T.; Gingrich, H. L.; Kam, C. K.; Mobraaten, E. C.; Jones, M., Jr. J. Am. Chem. Soc. 1991, 113, 1313-1318.
18. (c) Gingrich, H. L.; Ghosh, T.; Huang, Q.; Li, J.; Jones, M., Jr. Pure Appl. Chem. 1993, 65, 65-71.
19. (a) Jeon, J.; Kitamura, T.; Yoo, B.-W.; Kang, S. O.; Ko, J. Chem. Commun. 2001, 2110-2111.
20. (b) Lee, T.; Jeon, J.; Song, K. H.; Jung, I.; Baik, C.; Park, K.-M.; Lee, S. S.; Kang, S. O.; Ko, J. Dalton Trans. 2004, 933-937.
21. (a) Qiu, Z.; Wang, S. R.; Xie, Z. Angew. Chem., Int. Ed. 2010, 49, 4649-4652. For metal-carboryne chemistry developed in our lab, see:
22. (b) Deng, L.; Chan, H.-S.; Xie, Z. J. Am. Chem. Soc. 2006, 128, 7728-7729.
23. (c) Qiu, Z.; Xie, Z. Angew. Chem., Int. Ed. 2008, 47, 6572-6575.
24. (d) Qiu, Z.; Xie, Z. J. Am. Chem. Soc. 2009, 131, 2084-2085.
25. (e) Ren, S.; Chan, H.-S.; Xie, Z. J. Am. Chem. Soc. 2009, 131, 3862-3863.
26. (a) For experimental detail, complete characterization data, and X-ray data, see the Supporting Information.
27. (b) These [4+2] and [2+2] cycloaddition reactions are stereospecific reactions. Compounds 5c, 7e, and 8e were isolated as racemates.
28. Brinkley, J. M.; Friedman, L. Tetrahedron Lett. 1972, 13, 4141-4142.
29. The [2+2] cycloaddition reaction was observed in the reaction of thiophenes with both benzyne and carboryne; see: (a) Reinecke, M. G.; Mazza, D. D. J. Org. Chem. 1989, 54, 2142-2146.
30. (b) Barnett-Thamattoor, L.; Zheng, G.-X.; Ho, D. M.; Jones, M., Jr. Inorg. Chem. 1996, 35, 7311-7315.
31. (a) Cope, A. C.; Haven, A. C.; Ramp, F. L.; Trumbull, E. R. J. Am. Chem. Soc. 1952, 74, 4867-4871.
32. (b) Hulot, C.; Amiri, S.; Blond, G.; Schreiner, P. R.; Suffert, J. J. Am. Chem. Soc. 2009, 131, 13387-13398.