Intramolecular amine-induced [1,3]-sigmatropic rearrangement in the reactions of aminophosphinites or phosphites with elemental sulfur or selenium

Inorganic Chemistry

Volumn 45, Issue 15, 2006, Pages 5893-5897

  Chandrasekaran, P ^a   Mague, Joel T ^b   Balakrishna, Maravanji S ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746970445     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic060413m     Document Type: Article

References (67)

1. (a) Priya, S.; Balakrishna, M. S.; Mague, J. T.; Mobin, S. M. Inorg. Chem. 2003, 42, 1272-1281.
2. (b) Priya, S.; Balakrishna, M. S.; Mague, J. T. Inorg. Chem. Commun. 2001, 4, 437-440.
3. (c) Priya, S.; Balakrishna, M. S.; Mobin, S. M. Polyhedron 2005, 24, 1641-1650.
4. (a) Hoffmann, R. W. Angew. Chem., Int. Ed. 2001, 40, 1411-1416.
5. (b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
6. (a) Mugrage, B.; Diefenbacher, C.; Somers, J.; Parker, D. T.; Parker, T. Tetrahedron Lett. 2000, 41, 2047-2050.
7. (b) Malachowski, W. P.; Coward, J. K. J. Org. Chem. 1994, 59, 7625-7634.
8. (a) Dandapani, S.; Curran, D. P. Chem. - Eur. J. 2004, 10, 3130-3138.
9. (b) Satish Kumar, N.; Praveen Kumar, K.; Pavan Kumar, K. V. P.; Kommana, P.; Vittal, J. J.; Kumara Swamy, K. C. J. Org. Chem 2004, 69, 1880-1889.
10. (a) Chen, B.; Mapp, A. K. J. Am. Chem. Soc. 2004, 126, 5364-5365.
11. (b) Chen, B.; Mapp, A. K. J. Am. Chem. Soc. 2005, 127, 6712-6718.
12. Janecki, T.; Bodalski, R. Synthesis 1990, 799-801.
13. Lee, E. E.; Bately, R. A. Angew. Chem., Int. Ed. 2004, 43, 1865-1868.
14. Nuretdinov, I. A.; Buina, N. A.; Bayandika, E. V. Zh. Obshch. Khim. 1978, 48, 1073-1078.
15. (a) Kimura, T.; Murai, T.; Mizuhata, N. Heteroat. Chem. 2005, 16, 185-191.
16. (b) Darmadi, A.; Haas, A.; Kaschani-Motlagh, M. Z. Anorg. Allg. Chem. 1979, 448, 35-39.
17. (a) Kimura, T.; Murai, T. J. Org. chem. 2005, 70, 952-959.
18. (b) Stec, W. J.; Okrusecek, A.; Lesiak, K.; Uznanski, B.; Michalski, J. J. Org. Chem. 1976, 41, 227-233.
19. (a) Stahl, L. Coord. Chem. Rev. 2000, 210, 203-250.
20. (b) Chivers, T.; Krahn, M.; Parvez, M. Chem. Commun. 2000, 463-464.
21. (c) Chivers, T.; Fedorchuk, C.; Krahn, M.; Parvez, M.; Schatte, G. Inorg. Chem. 2001, 40, 1936-1942.
22. (d) Chivers, T.; Krahn, M.; Parvez, M.; Schatte, G. Inorg. Chem. 2001, 40, 2547-2553.
23. (e) Briand, G. G.; Chivers, T.; Parvez, M.; Schatte, G. Inorg. Chem. 2003, 42, 525-531.
24. (a) Balakrishna, M. S.; Reddy, V. S.; Krishnamurthy, S. S.; Nixon, J. F.; Laurent, J. C. T. R. B. S. Coord. Chem. Rev. 1994, 129, 1-90.
25. (b) Reddy, V. S.; Krishnamurthy, S. S.; Nethaji, M. J. Chem. Soc., Dalton Trans. 1995, 1933-1938.
26. (c) Briand, G. G.; Chivers, T.; Krahn, M. Coord. Chem. Rev. 2002, 233-234, 237-254.
27. (d) Chivers, T.; Krahn, M.; Parvez, M.; Schatte, G. Inorg. Chem. 2001, 40, 2547-2553.
28. (e) Schranz, I.; Lief, G. R.; Carrow, C. J.; Haagenson, D. C.; Grocholl, L.; Stahl, L.; Staples, R. J.; Boomishankar, R.; Steiner, A. Dalton Trans. 2005, 3307-3318.
29. (f) Lief, G. R.; Moser, D. F.; Stahl, L.; Staples, R. J. J. Organomet. Chem. 2004, 689, 1110-1121.
30. (g) Lief, G. R.; Carrow, C. J.; Stahl, L.; Staples, R. J. Chem. Commun. 2001, 1562-1563.
31. (a) Burford, N.; Cameron, T. S.; Lam, K. C.; LeBlanc, D. J.; McDonald, C. L. B.; Philips, A. D.; Rheingold, A. L.; Stark, L.; Walsh, D. Can. J. Chem. 2001, 79, 342-348.
32. (b) Burford, N.; Cameron, T. S.; Conroy, K. D.; Ellis, B.; MacDonald, C. L. B.; Ovans, R.; Phillips, A. D.; Ragogna, P. J.; Walsh, D. Can. J. Chem. 2002, 80, 1404-1409.
33. (c) Burford, N.; Cameron, T. S.; Conroy, K. D.; Ellis, B.; Lumsden, M.; Macdonald, C. L. B.; McDonald, R.; Phillips, A. D.; Ragogna, P. J.; Schurko, R. W.; Walsh, D.; Wasylishen, R. E. J. Am. Chem. Soc. 2002, 124, 14012-14013.
34. (d) Burford, N.; Dyker, C. A.; Phillips, A. D.; Spinney, H. A.; Deckon, A.; McDonald, R.; Ragogna, P. J.; Rheingold, A. L. Inorg. Chem. 2004, 43, 7502-7507.
35. (e) Burford, N.; Edelstein, E.; Landry, J. C.; Ferguson, M. J.; McDonald, R. Chem. Commun. 2005, 5074-5076.
36. (f) Burford, N.; Conroy, K. D.; Landry, J. C.; Ragogna, P. J.; Ferguson, M. J.; McDonald, R. Inorg. Chem. 2004, 43, 8245-8251.
37. (g) Garcia, F.; Kowenicki, R. A.; Riera, L.; Wright, D. S. Dalton Trans. 2005, 2495-2496.
38. (a) Kumaravel, S. S.; Krishnamurthy, S. S.; Cameron, T. S.; Linden, A. Inorg. Chem. 1988, 27, 4546-4550.
39. (b) Kommana, P.; Vittal, J. J.; Kumara Swamy, K. C. Polyhedron 2003, 22, 843-847.
40. (c) Kommana, P.; Kumara Swamy, K. C. Inorg. Chem. 2000, 39, 4384-4385.
41. (d) Dodds, F.; Garcia, F.; Kowenicki, R. A.; McPartlin, M.; Steiner, A.; Wright, D. S. Chem. Commun. 2005, 3733-3735.
42. (e) Dodds, F.; Garcia, F.; Kowenicki, R. A.; McPartlin, M.; Riera, L.; Steiner, A.; Wright, D. S. Chem. Commun. 2005, 5041-5043.
43. (f) Doyle, E. L.; Riera, L.; Wright, D. S. Eur. J. Inorg. Chem. 2003, 3279-3289.
44. (g) Doyle, E. L.; Garcia, F.; Humprey, S. M.; Kowenicki, R. A.; Riera, L.; Woods, A. D.; Wright, D. S. Dalton Trans. 2004, 807-812.
45. (h) Garcia, F.; Goodman, J. M.; Kowenicki, R. A.; McPartlin, M.; Riera, L.; Silva, M. A.; Wirsing, A.; Wright, D. S. Dalton Trans. 2005, 1764-1773.
46. (i) Garcia, F.; Kowenicki, R. A.; Kuzu, I.; Riera, L.; McPartlin, M.; Wright, D. S. Dalton Trans. 2004, 2904-2909.
47. (a) Chandrasekaran, P.; Mague, J. T.; Balakrishna, M. S. Organometallics 2005, 24, 3780-3783.
48. (b) Chandrasekaran, P.; Mague, J. T.; Balakrishna, M. S. Inorg. Chem. 2005, 44, 7925-7932.
49. Kimura, T.; Murai, T. J. Org. Chem. 2005, 70, 5611-5617.
50. Bandoli, G.; Bortolozzo, G.; Clemente, D. A.; Croatto, U.; Panattoni, C. J. Chem. Soc., A 1970, 2778-2780.
51. Rankin, D. W. H.; Robertson, H. E.; Seip, R.; Schmidbaur, H.; Blaschke, G. J. Chem. Soc., Dalton Trans. 1985, 827-830.
52. Sase, S.; Kano, N.; Kawashima, T. J. Am. Chem. Soc. 2002, 124, 9706-9707.
53. (a) Silaghi-Dumitrescu, I.; Haiduc, I. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 91, 21-36.
54. (b) Dutasta, J. P.; Declercq, J. P.; Calderon, C. E.; Tinant, B. J. Am. Chem. Soc. 1989, 111, 7136-7144.
55. Challis, B. C.; Challis, J. A.; Iley, J. N. J. Chem. Soc., Perkin Trans. 2 1978, 813-818.
56. (a) Kumar, S.; Kandasamy, K.; Singh, H. B.; Butcher, R. J. Organometallics 2004, 23, 4199-4208.
57. (b) Mugesh, G.; Singh, H. B. Chem. Soc. Rev. 2000, 29, 347-357.
58. (d) Iwaoka, M.; Tomoda, S. J. Am. Chem. Soc. 1996, 118, 8077-8084.
59. (a) Sanz, P.; Yanez, M.; Mo, O. Chem. - Eur. J. 2003, 9, 4548-4555.
60. (b) Sanz, P.; Yanez, M.; Mo, O. J. Phy. Chem. A 2002, 106, 4661-4668.
61. (c) Bleiholder, C.; Werz, D. B.; Koppel, H.; Gleiter, R. J. Am. Chem. Soc. 2006, 128, 2666-2674.
62. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, 4th ed.; Butterworth-Heinemann Linacre House: Jordan Hill, Oxford, U.K., 1996.
63. SMART, version 5.625; Bruker-AXS: Madison, WI, 2000.
64. SAINT+, version 6.35A; Bruker-AXS: Madison, WI, 2002.
65. Sheldrick, G, M. SADABS, version 2.05; University of Göttingen; Göttingen, Germany, 2002.
66. SHELXTL, version 6.10; Bruker-AXS: Madison, WI, 2000.
67. (b) Sheldrick, G. M. SHELXS97 and SHELXL97; University of Göttingen: Göttingen, Germany, 1997.