Characterization of cyclopentyllithium and cyclopentyllithium tetrahydrofuran complex

Journal of the American Chemical Society

Volumn 135, Issue 33, 2013, Pages 12400-12406

  Su, Chicheung ^a   Hopson, Russell ^a   Williard, Paul G ^a  

^a BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CORRELATION ANALYSIS; HYDROCARBON SOLVENTS; ONE-AND TWO-DIMENSIONAL NMR; SINGLE CRYSTAL X-RAY DIFFRACTION; SOLID-STATE STRUCTURES; TETRA-HYDROFURAN; TETRAMERIC; TETRAMERS;

DIFFUSION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY DIFFRACTION;

OLIGOMERS;

CYCLOPENTYLLITHIUM; CYCLOPENTYLLITHIUM TETRAHYDROFURAN COMPLEX; HYDROCARBON; LITHIUM DERIVATIVE; METAL COMPLEX; TETRAHYDROFURAN DERIVATIVE; TETRAMER; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTALLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLVATION; X RAY DIFFRACTION;

EID: 84883058722     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4059102     Document Type: Article

References (74)

1. Rappoport, Z. and Marek, I., Eds. The Chemistry of Organolithium Compounds; John Wiley & Sons, Ltd.: West Sussex, UK, 2004.
2. Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon: Oxford, UK, 2002.
3. Hodgson, D. Organolithiums in Enantionselective Synthesis; Springer: New York, 2003.
4. Trost, B. M. and Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon: Oxford, UK, 1991.
5. Wu, G.; Huang, M. Chem. Rev. 2006, 106, 2596-2616
6. Collum, D. B.; McNeil, A. J.; Ramirez, A. Angew. Chem., Int. Ed. 2007, 46, 3002-3017
7. Lucht, B.; Collum, D. Acc. Chem. Res. 1999, 32, 1035-1042
8. Snieckus, V. Chem. Rev. 1990, 90, 879-933
9. Evans, D. A.; Andrews, G. C. Acc. Chem. Res. 1974, 7, 147-155
10. Still, W. C.; Macdonald, T. L. J. Am. Chem. Soc. 1974, 96, 5561-5563
11. Carbone, G.; O'Brien, P.; Hilmersson, G. J. Am. Chem. Soc. 2010, 132, 15445-15450
12. Coldham, I.; Leonori, D. Org. Lett. 2008, 10, 3923-3925
13. Wu, S.; Lee, S.; Beak, P. J. Am. Chem. Soc. 1996, 118, 715-721
14. Lutz, G. P.; Du, H.; Gallagher, D. J.; Beak, P. J. Org. Chem. 1996, 61, 4542-4554
15. Herbert, S. A.; Arnott, G. E. Org. Lett. 2009, 11, 4986-4989
16. Crandall, J. K.; Clark, A. C. J. Org. Chem. 1972, 37, 4236-4242
17. Al-Aseer, M. A.; Allison, B. D.; Smith, S. G. J. Org. Chem. 1985, 50, 2715-2719
18. Schrock, R. R.; Shih, K.; Dobbs, D. A.; Davis, W. M. J. Am. Chem. Soc. 1995, 117, 6609-6610
19. Schrock, R. R.; Seidel, S. W.; Mosch-Zanetti, N. C.; Dobbs, D. A.; Shih, K.; Davis, W. M. Organometallics 1997, 16, 5195-5200
20. Weber, L.; Meyer, M.; Stammler, H.; Neumann, B. Organometallics 2003, 22, 5063-5068
21. Toba, T.; Murata, K.; Futamura, J.; Nakanishi, K.; Takahashi, B.; Takemoto, N.; Tomino, M.; Nakatsuka, T.; Imajo, S.; Goto, M.; Yamamura, T.; Miyake, S.; Annoura, H. Bioorg. Med. Chem. 2012, 20, 2850-2859
22. Chai, G.; Fu, C.; Ma, S. Org. Lett. 2012, 14, 4058-4061
23. Green, J. C.; Brown, E. R.; Pettus, T. R. R. Org. Lett. 2012, 14, 2929-2931
24. Narayan, R.; Frohlich, R.; Wurthwein, E. J. Org. Chem. 2012, 77, 1868-1897
25. Fournier, A. M.; Clayden, J. Org. Lett. 2012, 14, 142-145
26. Tait, M.; Donnard, M.; Minassi, A.; Lefranc, J.; Bechi, B.; Carbone, G.; O'Brien, P.; Clayden, J. Org. Lett. 2013, 15, 34-37
27. West, P.; Waack, R.; Purmort, J. I. J. Am. Chem. Soc. 1970, 92, 840-845
28. McGarrity, J. F.; Ogle, C. A.; Brich, Z.; Loosli, H. J. Am. Chem. Soc. 1985, 107, 1810-1815
29. Bates, T. F.; Clarke, M. T.; Thomas, R. D. J. Am. Chem. Soc. 1988, 110, 5109-5112
30. Ogle, C. A.; Johnson, H. C., IV; Wang, X. L.; Strickler, F. H.; Bucca, D.; Gordon, B., III Macromolecules 1995, 28, 5184-5191
31. Lucht, B. L.; Bernstein, M. P.; Remenar, J. F.; Collum, D. B. J. Am. Chem. Soc. 1996, 118, 10707-10718
32. Reich, H. J.; Green, D. P.; Medina, M. A.; Goldenberg, W. S.; Gudmundsson, B. O.; Dykstra, R. R.; Phillips, N. H. J. Am. Chem. Soc. 1998, 120, 7201-7210
33. Rutherford, J. L.; Hoffmann, D.; Collum, D. B. J. Am. Chem. Soc. 2002, 124, 264-271
34. Jones, A. C.; Sanders, A. W.; Bevan, M. J.; Reich, H. J. J. Am. Chem. Soc. 2007, 129, 3492-3493
35. Stanetty, P.; Mihovilovic, M. D. J. Org. Chem. 1997, 62, 1514-1515
36. Nichols, M. A.; Williard, P. G. J. Am. Chem. Soc. 1993, 115, 1568-1572
37. Barnett, N. D. R.; Mulvey, R. E.; Clegg, W.; O'Neil, P. A. J. Am. Chem. Soc. 1993, 115, 1573-1574
38. Ogle, C. A.; Huckabee, B. K.; Johnson, H. C. I. V.; Sims, P. F.; Winslow, S. D.; Pinkerton, A. A. Organometallics 1993, 12, 1960-1963
39. Kottke, T.; Lagow, R. J.; Hoffmann, D.; Thomas, R. D. Organometallics 1997, 16, 789-792
40. Klumpp, G. W.; Geurink, P. J. A.; Spek, A, L.; Duisenberg, A. J. M. Chem. Commun. (Cambridge, U.K.) 1983, 814-816
41. Spek, A. L.; Duisenberg, A. J. M.; Klumpp, G. W.; Geurink, P. J. A. Acta Crystallogr., Sect. C. 1984, C40, 372-374
42. Moene, W.; Vos, M.; De Kanter, F. J. J.; Klumpp, G. W.; Spek, A. L. J. Am. Chem. Soc. 1989, 111, 3463-3465
43. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853-1858
44. Williard, P. G.; Sun, C. J. Am. Chem. Soc. 1997, 119, 11693-11694
45. Strohmann, C.; Strohfeldt, K.; Schildbach, D. J. Am. Chem. Soc. 2003, 125, 13672-13673
46. Strohmann, C.; Gessner, V. H. J. Am. Chem. Soc. 2007, 129, 8952-8953
47. Strohmann, C.; Gessner, V. H.; Damme, A. Chem. Commun. (Cambridge, U.K.) 2008, 3381-3383
48. Kottke, T.; Stalke, D. Angew. Chem., Int. Ed. Engl. 1993, 32, 580-582
49. Siemeling, U.; Redecker, T.; Neumann, B.; Stammler, H. J. Am. Chem. Soc. 1994, 116, 5507-5508
50. Zerger, R.; Rhine, W.; Stucky, G. J. Am. Chem. Soc. 1974, 116, 6048-6055
51. Hoye, T. R.; Eklov, B. M.; Voloshin, M. Org. Lett. 2004, 6, 2567-2570
52. Wetzel, T. G.; Dehnen, S.; Roesky, P. W. Organometallics 1999, 18, 3835-3842
53. Gausing, W.; Wilke, G. Angew. Chem., Int. Ed. 1978, 17, 371-372
54. Fraenkel, G.; Henrichs, M.; Hewitt, M.; Su, B. M. J. Am. Chem. Soc. 1984, 106, 255-256
55. Su, C.; Hopson, R.; Williard, P. G. Eur. J. Inorg. Chem. 2013, 24, 4136-4141
56. Li, D.; Hopson, R.; Li, W.; Liu, J.; Williard, P. G. Org. Lett. 2008, 10, 909-911
57. Li, D.; Sun, C.; Williard, P. G. J. Am. Chem. Soc. 2008, 130, 11726-11736
58. Li, D.; Sun, C.; Liu, J.; Hopson, R.; Williard, P. G. J. Org. Chem. 2008, 73, 2373-2381
59. Liu, J.; Li, D.; Sun, C.; Williard, P. G. J. Org. Chem. 2008, 73, 4045-4052
60. Li, D.; Kagan, G.; Hopson, R.; Williard, P. G. J. Am. Chem. Soc. 2009, 131, 5627-5634
61. Li, D.; Keresztes, I.; Hopson, R.; Williard, P. G. Acc. Chem. Res. 2009, 42, 270-280
62. Kagan, G.; Li, W.; Hopson, R.; Williard, P. G. Org. Lett. 2009, 11, 4818-4821
63. Kagan, G.; Li, W.; Hopson, R.; Williard, P. G. Org. Lett. 2010, 12, 520-523
64. Li, W.; Kagan, G.; Yang, H.; Cai, C.; Hopson, R.; Sweigart, D. A.; Williard, P. G. Org. Lett. 2010, 12, 2698-2701
65. Li, W.; Kagan, G.; Yang, H.; Cai, C.; Hopson, R.; Dai, W.; Sweigart, D. A.; Williard, P. G. Organometallics 2010, 29, 1309-1311
66. Socha, A. M.; Kagan, G.; Li, W.; Hopson, R.; Sello, J. K.; Williard, P. G. Energy Fuels 2010, 24, 4518-4521
67. Kagan, G.; Li, W.; Sun, C.; Hopson, R.; Williard, P. G. J. Org. Chem. 2011, 76, 65-70
68. Kagan, G.; Li, W.; Li, D.; Hopson, R.; Williard, P. G. J. Am. Chem. Soc. 2011, 133, 6596-6602
69. Lecachey, B.; Oulyadi, H.; Lameiras, P.; Harrison-Marchand, A.; Gerard, H.; Maddaluno, J. J. Org. Chem. 2010, 75, 5976-5983
70. Consiglio, G. B.; Queval, P.; Harrison-Marchand, A.; Mordini, A.; Lohier, J.; Delacroix, O.; Gaumont, A.; Gerard, H.; Maddaluno, J.; Oulyadi, H. J. Am. Chem. Soc. 2011, 133, 6472-6480
71. Li, W.; Kagan, G.; Hopson, R.; Williard, P. G. ARKIVOC 2011, 180-187
72. Keresztes, I.; Williard, P. G. J. Am. Chem. Soc. 2000, 122, 10228-10229
73. McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805-1810
74. Smith, W. N. US Patent 3511884, 1970.