1,3-steric induction in intermolecular radical reactions mediated by a Co2(CO)6-metal core

Organometallics

Volumn 29, Issue 16, 2010, Pages 3556-3562

  Melikyan, Gagik G ^a   Spencer, Ryan ^a   Rowe, Aaron ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIYNES; AUXILIARY GROUPS; COUPLING PRODUCT; COUPLING REACTION; DIASTEREO-SELECTIVITY; METAL CORE; PROPARGYL; PROPARGYL RADICAL; RADICAL REACTIONS; SYNTHETIC STRATEGIES;

REACTION KINETICS;

X RAY CRYSTALLOGRAPHY;

EID: 77955700669     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100472y     Document Type: Article

References (39)

1. cis-/ trans-Hydrogenation: Larock, R. C. Comprehensive Organic Transformations: a Guide to Functional Group Preparations, 2 nd ed.; VCH: New York, 1999; p 405. Hydration of alkynes: Menashe, N.; Shvo, Y. J. Org. Chem. 1993, 58, 7434
2. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563 Synthesis of pyrroles: Ramanathan, B.; Keith, A. J.; Armstrong, D.; Odom, A. L. Org. Lett. 2004, 6, 2957 Intramolecular aldol condensation: Hayashi, Y.; Sekizawa, H.; Yamaguchi, J.; Gotoh, H. J. Org. Chem. 2007, 72, 6493, and references therein. Pinacol coupling: Kise, N.; Shiozawa, Y.; Ueda, N. Tetrahedron Lett. 2004, 45, 7599 Enediyne antibiotics: Smith, A. L.; Nicolaou, K. C. J. Med. Chem. 1996, 39, 2103 Transannular interactions: Wempe, M. F.; Grunwell, J. R. J. Org. Chem. 1995, 60, 2714
3. Gleiter, R.; Ritter, H.; Irngartinger, H.; Lichtenthaler, J. Tetrahedron Lett. 1991, 32, 2883 Fused carbocycles: Alvarez, E.; Diaz, M. T.; Perez, R.; Ravelo, J. L.; Regueiro, A.; Vera, J. A.; Zurita, D.; Martin, J. D. J. Org. Chem. 1994, 59, 2848
4. Badanyan, Sh. O.; Voskanyan, M. G.; Chobanyan, Zh. A. Russ. Chem. Rev. 1981, 50, 1074
5. Yang, F.; Zhao, G.; Ding, Y.; Zhao, Z.; Zheng, Y. Tetrahedron Lett. 2002, 43, 1289
6. Onodera, G.; Nishibayashi, Y.; Uemura, S. Organometallics 2006, 25, 35
7. Ogoshi, S.; Nishiguchi, S.; Tsutsumi, K.; Kurosawa, H. J. Org. Chem. 1995, 60, 4650
8. Melikyan, G. G.; Nicholas, K. M. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Eds.; VCH Publishers: Weinheim, 1995; Chapter 4.
9. McGlinchey, M. J.; Girard, L.; Ruffolo, R. Coord. Chem. Rev. 1995, 143, 331
10. Amouri, H. E.; Gruselle, M. Chem. Rev. 1996, 96, 1077
11. Went, M. Adv. Organomet. Chem. 1997, 41, 69
12. Green, J. R. Curr. Org. Chem. 2001, 5, 809
13. Muller, T. J. J. Eur. J. Org. Chem. 2001, 2021
14. Teobald, B. J. Tetrahedron 2002, 58, 4133
15. Melikyan, G. G.; Sepanian, S.; Riahi, B.; Villena, F.; Jerome, J.; Ahrens, B.; McClain, R.; Matchett, J.; Scanlon, S.; Abrenica, E.; Paulsen, K.; Hardcastle, K. I. J. Organomet. Chem. 2003, 683, 324
16. Melikyan, G. G.; Villena, F.; Sepanian, S.; Pulido, M.; Sarkissian, H.; Florut, A. Org. Lett. 2003, 5, 3395
17. Melikyan, G. G.; Villena, F.; Florut, A.; Sepanian, S.; Sarkissian, H.; Rowe, A.; Toure, P.; Mehta, D.; Christian, N.; Myer, S.; Miller, D.; Scanlon, S.; Porazik, M. Organometallics 2006, 25, 4680
18. Melikyan, G. G.; Floruti, A.; Devletyan, L.; Toure, P.; Dean, N.; Carlson, L. Organometallics 2007, 26, 3173
19. Melikyan, G. G.; Wild, C.; Toure, P. Organometallics 2008, 27, 1569
20. Melikyan, G. G.; Mikailian, B.; Sepanian, R.; Toure, P. J. Organomet. Chem. 2009, 694, 785
21. Melikyan, G. G.; Sepanian, R.; Spencer, R.; Rowe, A.; Toure, P. Organometallics 2009, 28, 5541
22. Melikyan, G. G.; Spencer, R.; Abedi, E. J. Org. Chem. 2009, 74, 8541
23. Melikyan, G. G.; Voorhees, E.; Wild, C.; Spencer, R.; Molnar, J. Tetrahedron Lett. 2010, 51, 2287
24. Melikyan, G. G.; Spencer, R. Tetrahedron 2010, 66, 5321
25. Mitchell, H. J.; Nelson, A.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1999, 1899
26. Mikami, K.; Shimizu, M.; Zhang, H.; Maryanoff, B. E. Tetrahedron 2001, 57, 2917
27. Hayashi, Y.; Yamaguchi, H.; Toyoshima, M.; Nasu, S.; Ochiai, K.; Shoji, M. Organometallics 2008, 27, 163
28. Melikyan, G. G.; Combs, R. C.; Lamirand, J.; Khan, M.; Nicholas, K. M. Tetrahedron Lett. 1994, 35, 363
29. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: New York, 1981; p 80.
30. Greenfield, H.; Sternberg, H. W.; Friedel, R. A.; Wotiz, J. H.; Markby, R.; Wender, I. J. Am. Chem. Soc. 1956, 78, 120
31. SMART Version 5.628; Bruker AXS, Inc., Analytical X-ray Systems: Madison, WI, 2003.
32. SAINT Version 6.36A; Bruker AXS, Inc., Analytical X-ray Systems: Madison, WI, 2002.
33. Sheldrick, G. SADABS Version 2.10; University of Göttingen, 2003.
34. Sheldrick, G. M. A short history of SHELX Acta Crystallogr. 2008, A64, 112
35. Wilson, A. J. C., Ed. International Tables for X-ray Crystallography, Vol. C; Kynoch, Academic Publishers: Dordrecht, 1992; Tables 6.1.1.4 (pp 500-502) and 4.2.6.8 (pp 219-222).
36. Alphonse, F.; Karim, R.; Cano-Soumillac, C.; Hebray, M.; Collison, D; Garner, D.; Joule, J. Tetrahedron 2005, 614, 11010
37. Bondi, A. J. Phys. Chem. 1964, 68, 441
38. Mantina, M.; Chamberlin, A. C.; Valero, R.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. A 2009, 113, 5806
39. 3.