Mechanistic studies on the cyclization of organosilicon and organotin compounds containing the O,C,O-coordinating pincer-type ligand {4-t-Bu-2,6-[P(O)(OR)2]2C6 H2}- (R = i-Pr, Et): Phosphorus (POC)-versus carbon (POC)-attack

Organometallics

Volumn 23, Issue 7, 2004, Pages 1501-1508

  Peveling, Katja ^a   Henn, Markus ^a   Löw, Christian ^a   Mehring, Michael ^a   Schürmann, Markus ^a   Costisella, Burkhard ^a   Jurkschat, Klaus ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; COORDINATION REACTIONS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PHOSPHORUS; SUBSTITUTION REACTIONS; WATER; X RAY DIFFRACTION ANALYSIS;

BENZOXAPHOSPHASILOLE; BENZOXAPHOSPHASTANNOLE; BERRY PSEUDOROTATION; BROMIDE; ELECTROSPRAY MASS SPECTROMETRY; FLUORIDE; INTRAMOLECULAR CYCLIZATION; NUCLEOPHILIC SUBSTITUTION; ORGANOSILICON COMPOUNDS; ORGANOTIN COMPOUNDS;

ORGANOMETALLICS;

EID: 1842690646     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0305061     Document Type: Article

References (44)

1. Mehring, M.; Jurkschat, K.; Schürmann, M. Main Group Met. Chem. 1998, 21, 635.
2. Peveling, K.; Schürmann, M.; Jurkschat, K. Main Group Met. Chem. 2001, 24, 251.
3. Peveling, K.; Schürmann, M.; Ludwig, R.; Jurkschat, K. Organometallics 2001, 20, 4654. In this paper the nomenclature used was not correct (for instance benzoaxisilaphosphole instead of benzoxaphosphasilole). We thank an anonymous reviewer for making us aware of this.
4. Mehring, M.; Schürmann, M.; Jurkschat, K. Organometallics 1998, 17, 1227.
5. Mehring, M.; Löw, C.; Schürmann, M.; Jurkschat, K. Eur. J. Inorg. Chem. 1999, 887.
6. Mehring, M.; Vrasidas, I.; Horn, D.; Schürmann, M.; Jurkschat, K. Organometallics 2001, 20, 4647.
7. Peveling, K.; Schürmann, M.; Jurkschat, K. Z. Anorg. Allg. Chem. 2002, 628, 2435.
8. Mickoleit, M. Synthese Struktur und Reaktivität donorstabilisierter Silene. Dissertation Universität Rostock, Rostock, Germany, 2002.
9. Kost, D.; Gostevskii, B.; Kocher, N.; Stalke, D.; Kalikhman, I. Angew. Chem. 2003, 115, 1053
10. Angew. Chem., Int. Ed. 2003, 42, 1023.
11. Berlekamp, U. H.; Mix, A.; Jutzi, P.; Stammler, H. G.; Neumann, B. Oxygen, Phosphorus or Sulfur Donor Ligands in Higher-Coordinated Organosilyl Chlorides and Triflates. In Organosilicon Chemistry IV; Auner, N., Weiss, J., Eds.; Wiley-VCH: New York, 2000; p 489.
12. Kolb, U.; Dräger, M.; Jousseaume, B. Organometallics 1991, 10, 2737.
13. Kolb, U.; Beuter, M.; Dräger, M. Inorg. Chem. 1994, 33, 4522.
14. Kolb, U.; Beuter, M.; Gerner, M.; Dräger, M. Organometallics 1994, 13, 4413.
15. Mehring, M.; Löw, C.; Schürmann, M.; Uhlig, F.; Jurkschat, K.; Mahieu, B. Organometallics 2000, 19, 4613.
16. Pauling, L. The Nature of the Chemical Bond, 3rd ed.; Cornell University Press: Ithaca, New York, 1960.
17. Dunitz, J. D. X-Ray Analysis and the Structure of Organic Molecules; Cornell University Press: Ithaca, New York, 1979.
18. Huheey, J.; Keiter, E. A.; Keiter, R. L. Anorganische Chemie: Prinzipien von Struktur und Reaktivität, 2 ed.; de Gruyter: New York, 1995.
19. Henn, M.; Jurkschat, K.; Ludwig, R.; Mehring, M.; Peveling, K.; Schürmann, M. Z. Anorg. Allg. Chem. 2002, 628, 2940.
20. Lange, I.; Henschel, D.; Wirth, A.; Krahl, J.; Blaschette, A.; Jones, P. G. J. Organomet. Chem. 1995, 503, 155.
21. Kolb, U.; Dräger, M.; Dargatz, M.; Jurkschat, K. Organometallics 1995, 14, 2827.
22. Jastrzebski, J. T. B. H.; van Der Schaaf, P. A.; Boersma, J.; van Koten, G.; De Ridder, D. J. A.; Heijdenrijk, D. Organometallics 1992, 11, 1521.
23. Kyba, E. P. J. Am. Chem. Soc. 1975, 97, 2554.
24. Kyba, E. P. J. Am. Chem. Soc. 1976, 98, 4805.
25. Corriu, R. J. P.; Dutheil, J. P.; Lanneau, G. F.; Ould-Kada, S. Tetrahedron 1979, 35, 2889.
26. Corriu, R. J. P.; Lanneau, G. F.; Leclercq, D. Tetrahedron 1980, 36, 1617.
27. Corriu, R. J. P.; Dutheil, J. P.; Lanneau, G. F. Tetrahedron 1981, 37, 3681.
28. Corriu, R. J. P.; Dutheil, J. P.; Lanneau, G. F. J. Am. Chem. Soc. 1984, 106, 1060.
29. Corriu, R. J. P.; Lanneau, G. F.; Leclercq, D. Tetrahedron 1986, 42, 5591.
30. Westheimer, F. H. Acc. Chem. Res. 1968, 1, 70.
31. Braun, S.; Kalinowski, H.-O.; Berger, S. 150 and More Basic NMR Experiments; Wiley-VCH: New York, 1998.
32. Henn, M.; Jurkschat, K.; Mahieu, B.; Mehring, M.; Müller, D.; Schürmann, M. Manuscript to be published.
33. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millian, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Bomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian Inc.: Pittsburgh, 1998.
34. Buntine, M. A.; Hall, V. J.; Kosovel, F. J.; Tiekink, E. R. T. J. Phys. Chem. A 1998, 102, 2472.
35. Obora, Y.; Nakanishi, M.; Tokunaga, M.; Tsuji, Y. J. Org. Chem. 2002, 67, 5835.
36. Ryner, M.; Finne, A.; Albertsson, A.-C.; Kricheldorf, H. R. Macromolecules 2001, 34, 7281.
37. Hu, Y.-H.; Su, M.-D. J. Phys. Chem. A 2003, 107, 4130.
38. Tani, K.; Kato, S.; Kanda, T.; Inagaki, S. Org. Lett. 2001, 3, 655.
39. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
40. King, B. F.; Weinhold, F. J. Chem. Phys. 1995, 103, 333.
41. NBO 4.0 Program Manual; University of Wisconsin Theoretical Chemistry Institute Technical Report WISC-TCI-756.
42. Sheldrick, G. M. Acta Crystallogr. A 1990, 46, 467.
43. Sheldrick, G. M. SHELXL97; University of Göttingen: Germany, 1997.
44. International Tables for Crystallography; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992; Vol. C.