Synthesis of 1-stannacyclopent-3-enes and their pyrolysis to stannylenes

Organometallics

Volumn 28, Issue 8, 2009, Pages 2595-2608

  Zhou, Dong ^a,c   Reiche, Clemens ^a   Nag, Mrinmoy ^a   Soderquist, John A ^b   Gaspar, Petet P ^a  

^a WASHINGTON UNIVERSITY   (United States)

^b UNIVERSITY OF PUERTO RICO RIO PIEDRAS   (Puerto Rico)

^c WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION PARAMETER; FIRST-ORDER; HIGH YIELD; KINETIC STUDY; MAGNESIUM COMPLEXES; STANNYLENE; STANNYLENES; TETRAMETHYL; UNIMOLECULAR DISSOCIATION;

DISSOCIATION; MAGNESIUM; OLIGOMERIZATION; PYROLYSIS; SYNTHESIS (CHEMICAL);

TIN;

EID: 65749110918     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800541f     Document Type: Article

References (60)

1. A search of Chemical Abstracts files located only 17 distinct structures, of which all but three (1d, 1e, and 1j) resulted from stannylene addition to dienes:(a) Iwamoto, T.; Masuda, H.; Ishida, S.; Kabuto, C.; Kira, M. J. Organomet. Chem. 2004, 689, 1337.
2. Neale, N. R.; Tilley, T. D. J. Am. Chem. Soc. 2002, 124, 3802.
3. Setaka, W.; Sakamoto, K.; Kira, M.; Power, P. P. Organometallics 2001, 20, 4460.
4. Fañaná,F.J.; Granados, A.; Sanz, R.; Ignacio, J. M.; Barluenga, J. Chem.-Eur. J. 2001, 7, 2896.
5. Soderquist, J. A.; Leon, G. Tetrahedron Lett. 1998, 39, 2511.
6. Saito, M.; Tokitoh, N.; Okazaki, R. Organometallics 1996, 15, 4531.
7. Saito, M.; Tokitoh, N.; Okazaki, R. Chem. Lett. 1996, 265
8. Weidenbruch, M.; Stilter, A.; Schlaefke, J.; Peters, K.; von Schnering, H. G. J. Organomet. Chem. 1995, 501, 67.
9. Saito, M.; Tokitoh, N.; Okazaki, R. Organometallics 1995, 14, 3620.
10. Wrackmeyer, B.; Klaus, U.; Millius, W. Chem. Ber. 1995, 128, 679.
11. Tokitoh, N.; Saito, M.; Okazaki, R. J. Am. Chem. Soc. 1993, 115, 2065.
12. Gruetzmacher, H.; Freitag, S.; Herbst-Irmer, R.; Sheldrick, G. M. Angew. Chem., Int. Ed. Engl. 1992, 31, 437.
13. Weidenbruch, M.; Schaefer, A.; Kilian, H.; Pohl, S.; Saak, W.; Marsmann, H. Chem. Ber. 1992, 125, 563-566.
14. Marx, R.; Neumann, W. P.; Hillner, K. Tetrahedron Lett. 1984, 25, 625.
15. Dimethylsilylene: Lei, D.; Gaspar, P. P. Organometallics 1985, 4, 1471.
16. Dimethylgermylene: Lei, D.; Gaspar, P. P. Polyhedron 1991, 10, 1221.
17. Grugel, C.; Neumann, W. P.; Schriewer, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 543.
18. Neumann, W. P. Chem. Rev. 1991, 91, 311.
19. Atwell, W. H.; Weyenberg, D. R. J. Oreanomet. Chem. 1966, 5, 594.
20. J. Am. Chem. Soc. 1968, 90, 3438.
21. Schröer, U.; Neumann, W. P. Aneew. Chem., Int. Ed. Enel. 1975, 14, 246.
22. Cotton, J. D.; Davidson, P. J.; Lappert, M. F. J. Chem. Soc., Dalton Trans. 1976, 2275.
23. Weidenbruch, M.; Schäfer, A.; Kilian, H.; Pohl, S.; Saak, W.; Marsmann, H. Chem. Ber. 1991, 125, 563.
24. Masamune, S.; Sita, L. R. J. Am. Chem. Soc. 1985, 107, 6390.
25. Kira, M.; Yauchibara, R.; Hirano, R.; Kabuto, C.; Sakurai, H. J.Am. Chem. Soc. 1991, 113, 7785.
26. Kira, M.; Ishida, S.; Iwamoto, T. Chem. Rec. 2004, 4, 243.
27. Eaborn, C.; Hill, M. S.; Hitchcock, P. B.; Patel, D.; Smith, J. D.; Zhang, S. Organometallics 2000, 19, 49.
28. Asadi, A.; Eaborn, C.; Hill, M. S.; Hitchcock, P. B.; Meehan, M. M.; Smith, J. D. Oreanometallics 2002, 21, 2430.
29. Saito, M.; Tokitoh, N.; Okazaki, R. Organometallics 1996, 15, 4531.
30. Setaka, W.; Sakamoto, K.; Kira, M.; Power, P. P. Oreanometallics 2001, 20, 4460.
31. Fujita, K.; Ohnuma, Y.; Yasuda, H. J. Organomet. Chem. 1976, 113, 201.
32. Richter, W. J. Synthesis 1982, 12, 1102.
33. Jiang, P.; Gaspar, P. P. J. Am. Chem. Soc. 2001, 123, 8622.
34. Becerra, R.; Gaspar, P. P.; Harrington, C. R.; Leigh, W. J.; Vargas-Baca, I.; Walsh, R.; Zhou, D. J. Am. Chem. Soc. 2005, 127, 17469.
35. Watta, B.; Neumann, W. P.; Sauer, J. Organometallics 1985, 4, 1954.
36. Drager, M.; Mathiasch, B.; Ross, L.; Ross, M. Z. Anors. Alls. Chem. 1983, 506, 99.
37. Neumann, W. P.; Pedain, J.; Sommer, R. Ann. Chem. 1966, 694
38. Grugel, C.; Neumann, W. P.; Seifert, P. Tetrahedron Lett. 1977, 18, 2205.
39. Billeb, G.; Neumann, W. P.; Steinhoff, G. Tetrahedron Lett. 1988, 29, 5245.
40. Johnson, F.; Gohlke, R. S.; Nasulavicus, W. A. J. Organomet. Chem. 1965, 3, 233.
41. Vol'pin, M. E.; Struchkov, Yu.T.; Vilkov, L. V.; Mastryukov, V. S.; Dulova, V. G.; Kusanov, D. N. Izv. Akad. Nauk. SSSR, Ser. Khim. 1963, 2067.
42. Johnson, F.; Gohlke, R. S. Tetrahedron Lett. 1962, 1291.
43. Dewar, M. J. S.; Friedheim, J. E.; Grady, G. L. Organometallics 1985, 4, 1784.
44. 2, M = Si, Ge, Sn] and its reverse retro-addition reaction. Organometallics, in preparation.
45. Gross, L. W.; Moser, R.; Neumann, W. P.; Scherping, K. H. Tetrahedron Lett. 1975, 23, 635.
46. Finholt, A. E.; Bond, A. C.; Wilzbach, K. E.; Schlesinger, H. J. Am. Chem. Soc. 1947, 69, 2692.
47. Birchall, T.; Pereira, A. R. J. Chem. Soc., Dalton Trans. 1975, 1087.
48. Jones, J.; Lappert, M. F. J. Chem. Soc. 1965, 1944.
49. Kofron, W.; Baclawski, L. M. J. Org. Chem. 1976, 41, 1879.
50. van den Berghe, E. V.; van der Kelen, G. P. J. Organomet. Chem. 1973, 61, 197.
51. Fujita, K.; Ohnuma, Y.; Yasuda, H.; Tani, H. J^Organomet^Chem. 1976, 113, 201.
52. Rieke, R. D.; Xiong, H. J. Org. Chem. 1991, 56, 3109.
53. Unpublished data of J. A. Soderquist.
54. Jiang, P. Doctoral Dissertation, Washington University, St. Louis, 2002.
55. Marvel, C. S.; Woolford, R. G. J. Org. Chem. 1958, 23, 1658.
56. Schmidt, M.; Dersin, H. J.; Schumann, H. Chem. Ber. 1962, 95, 1428.
57. Farrar, W. V.; Skinner, H. A. J. Organomet. Chem. 1964, 1, 434.
58. Adams, S.; Drager, M. J. Organomet. Chem. 1985, 288, 295.
59. van den Berghe, E. V.; van der Kelen, G. P. J. Organomet. Chem. 1973, 59, 175.
60. Mitchell, T. N.; Walter, G. J. Chem. Soc., Perkin Trans. 2 1977, 1842.