Stereoselective synthesis of meso-1,5-cyclodecadiynes

Journal of Organic Chemistry

Volumn 74, Issue 22, 2009, Pages 8541-8546

  Melikyan, Gagik G ^a   Spencer, Ryan ^a   Abedi, Edwin ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COBALTOCENE; DECOMPLEXATIONS; PROPARGYL; STEREOSELECTIVE SYNTHESIS;

STEREOSELECTIVITY;

ALKYNE DERIVATIVE; COBALT COMPLEX; MESO 1,5 CYCLODECADIYNE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; DIYNES; HYDROCARBONS, CYCLIC; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 70449632714     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901404f     Document Type: Article

References (60)

1. (a) Gleiter, R.; Merger, R. In Modern Acetylene Chemistry; Stang P. J., Diederich F., Eds.; VCH Publishers: Weinheim, Germany, 1995; Chapter 8.
2. (b) Hirama, M. Pure Appl. Chem. 1997, 69, 525.
3. (c) Scott, L. T.; DeCicco, G. J.; Hyun, J. L.; Reinhardt, G. J. Am. Chem. Soc. 1985, 107, 6546.
4. (a) Lange, G. L.; Hall, T. J. Org. Chem. 1974, 39, 3819.
5. (b) Gleiter, R.; Kratz, D.; Schehlmann, V. Tetrahedron Lett. 1988, 29, 2813.
6. (c) Gleiter, R.; Kratz, D.; Schafer, W.; Schehlmann, V. J. Am. Chem. Soc. 1991, 113, 9258.
7. (a) Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry; Stang P. J., Diederich F., Eds.; VCH Publishers: Weinheim, Germany, 1995; Chapter 7, pp 203-283.
8. (b) Magnus, P. D. J. Am. Chem. Soc. 1995, 117, 12017.
9. (c) Kraka, E.; Cremer, D. J. Am. Chem. Soc. 2000, 122, 8245.
10. (d) Basak, A.; Mandal, S.; Bag, S. S. Chem. Rev. 2003, 103, 4077.
11. (e) Grissom, J.W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
12. (a) Iida, K.; Hirama, M. J. Am. Chem. Soc. 1994, 116, 10310.
13. (b)Wempe, M. F.; Grunwell, J. R. J. Org. Chem. 1995, 60, 2714.
14. (c) Gleiter, R.; Ritter, J.; Irngartinger, H.; Lichtenthaler, J. Tetrahedron Lett. 1991, 32, 2883.
15. Gleiter, R.; Schafer, W. Acc. Chem. Res. 1990, 23, 369.
16. Melikyan, G. G.; Combs, R. C.; Lamirand, J.; Khan, M.; Nicholas, K. M. Tetrahedron Lett. 1994, 363.
17. Melikyan, G. G.; Wild, C.; Toure, P. Organometallics 2008, 27, 1569.
18. (a) Melikyan, G. G.; Deravakian, A.; Myer, S.; Yadegar, S.; Hardcastle, K. I.; Ciurash, J.; Toure, P. J. Organomet. Chem. 1999, 578, 68.
19. (b) Melikyan, G. G.; Khan, M. A.; Nicholas, K. M. Organometallics 1995, 14, 2170.
20. (a) Mahler, J. E.; Gibson, D. H.; Pettit, R. J. Am. Chem. Soc. 1963, 85, 3959.
21. (b) Sapienza, R. S.; Riley, P. E.; Davis, R. E.; Pettit, R. J. Organomet. Chem. 1976, 121, C35.
22. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: New York, 1981; p 80.
23. Greenfield, H.; Sternberg, H. W.; Friedel, R. A.; Wotiz, J. H.; Markby, R.; Wender, I. J. Am. Chem. Soc. 1956, 78, 120.
24. (a) Muller, T. J. J. Eur. J. Org. Chem. 2001, 2021.
25. (b) Teobald, B. J. Tetrahedron 2002, 58, 4133.
26. (c) Melikyan, G. G.; Nicholas, K. M. In Modern Acetylene Chemistry; Stang P. J., Diederich F., Eds.; VCH Publishers:Weinheim, Germany, 1995; Chapter 4.
27. Larger excess of cobaltocene, up to 100 equiv, resulted in a rapid decomposition of the cyclized products, allegedly because of the overreduction of metal cores.
28. (a) Tyler, D. R. Acc. Chem. Res. 1991, 24, 325.
29. (b) Zavarine, I. S.; Kubiak, C. P. Coord. Chem. Rev. 1998, 171, 419. For the X-ray structure of cobaltocene see:
30. (c) Antipin, M. Yu.; Boese, R.; Augart, N.; Schmid, G. Struct. Chem. 1993, 4, 91.
31. Dickson, R. S.; Fraser, P. J. Advances in Organometallic Chemistry 12; Academic Press: New York, 1974; p 323.
32. (a) McGlinchey, M. J.; Girard, L.; Ruffolo, R. Coord. Chem. Rev. 1995, 143, 331.
33. (b) Amouri, H. E.; Gruselle, M. Chem. Rev. 1996, 96, 1077.
34. (c) Went, M. Adv. Organomet. Chem. 1997, 41, 69.
35. 2-1,10-bis(3′,4′- dimethoxyphenyl)-2,8-decadiyne]bis- (dicobalthexacarbonyl) (16) was formed as a side product, supposedly by the H-atomabstraction from methylene chloride. Its structure was confirmed by independent synthesis by quenching bis-cation 6 with tributyltinhydride.
36. (a) APEX II, Bruker AXS, Inc., Analytical X-ray Systems, 5465 East Cheryl Parkway, Madison, WI 53711-55373, 2005.
37. (b) SAINT, Version 6.45A, Bruker AXS, Inc., Analytical X-ray Systems, 5465 East Cheryl Parkway, Madison, WI 53711-55373, 2003.
38. (c) A short history of SHELX: Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122.
39. (d) Wilson, A. J. C., Ed. International Tables for X-ray Crystallography; Kynoch: Birmingham, England, 1992; Vol.C, Tables 6.1.1.4 (pp 500-502) and 4.2.6.8 (pp 219-222).
40. Mingos, D. M. P. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; N.-Y.; Pergamon: New York, 1982; Vol.3, p 1.
41. (a) Organometallic Radical Processes; Trogler, W. C., Ed.; Elsevier: Amsterdam, The Netherlands, 1990; Chapters 3, 4, 9, and 10.
42. (b) Astruc, D. Acc. Chem. Res. 1991, 24, 36.
43. (c) Astruc, D. Electron Transfer and Radical Processes in Transition-Metal Chemistry; VCH: New York, 1995; Chapters 3, 5, and 6.
44. (d) Torraca, K. E.; McElwee-White, L. Coord. Chem. Rev. 2000, 206-207, 469.
45. (e) Melikyan, G. G. In Frontiers in Organometallic Chemistry; Cato, M. A., Ed.; Nova Science Publishers: New York, 2006; p 155.
46. (a) Melikyan, G. G.; Deravakian, A. J. Organomet. Chem. 1997, 544, 143.
47. (b) Melikyan, G. G.; Bright, S.; Monroe, T.; Hardcastle, K. M.; Ciurash, J. Angew. Chem., Int. Ed. 1998, 37, 161.
48. (c) 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.
49. (d) Melikyan, G. G.; Villena, F.; Sepanian, S.; Pulido, M.; Sarkissian, H.; Florut, A. Org. Lett. 2003, 5, 3395.
50. (e) 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.
51. (f) Melikyan, G. G.; Floruti, A.; Devletyan, L.; Toure, P.; Dean, N.; Carlson, L. Organometallics 2007, 26, 3173.
52. (g) Melikyan, G. G.; Mikailian, B.; Sepanian, R.; Toure, P. J. Organomet. Chem. 2009, 694, 785.
53. 3: (a) Pearson, A. J.; Chen, Y.-S.; Daroux, M. L.; Tanaka, A. A.; Zettler, M. J. Chem. Soc., Chem. Commun. 1987, 155.
54. 4:
55. 3:
56. (d) Top, S.; Jaouen, G. J. Organomet. Chem. 1987, 336, 143. Ferrocenyl radical:
57. (e) Cais, M.; Eisenstadt, A. J. Chem. Soc. 1965, 30, 1148.
58. 9)-radical:
59. 6:
60. (h) Padmanabhan, S.; Nicholas, K. M. J. Organomet. Chem. 1981, 212, 115.