Synthesis and structure of cis-1,4-di(1-pyrenyl)decamethylcyclohexasilane

Organometallics

Volumn 22, Issue 11, 2003, Pages 2249-2258

  Kaats Richters, Veronica E M ^a   Cleij, Thomas J ^a,c   Jenneskens, Leonardus W ^a   Lutz, Martin ^b   Spek, Anthony L ^b   Van Walree, Cornelis A ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

^c LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; ISOMERS; MIXTURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

CYCLOHEXASILANES; DIPYRENYLDECAMETHYLCYCLOHEXASILANE; PYRENYLLITHIUM; X RAY CRYSTAL STRUCTURES;

ORGANOMETALLICS;

EID: 0037587292     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020980r     Document Type: Article

References (45)

1. Miller, R. D; Michl, J. Chem. Rev. 1989, 89, 1359.
2. Sekiguchi, A.; Nanjo, M.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1995, 117, 4195.
3. Lambert, J. B.; Pflug, J. L.; Stern, C. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 98.
4. Suzuki, H.; Kimata, Y.; Satoh, S.; Kuriyama, A. Chem. Lett. 1995, 293.
5. Bianconi, P. A.; Weidman, T. W. J. Am. Chem. Soc. 1988, 110, 2342.
6. Bianconi, P. A.; Schilling, F. C.; Weidman, T. W. Macromolecules 1989, 22, 1697.
7. van Walree, C. A.; Cleij, T. J.; Jenneskens, L. W.; Vlietstra, E. J.; van der Laan, G. P.; de Haas, M. P.; Lutz, E. T. G. Macromolecules 1996, 29, 7362.
8. Cliej, T. J.; Tsang, S. K. Y.; Jenneskens, L. W. Macromolecules 1999, 32, 3286.
9. Maxka, J.; Chrusciel, J.; Sasaki, M.; Matyjaszewski, K. Macromol. Symp. 1994, 77, 79.
10. Brough, L. F.; West, R. J. Am. Chem. Soc. 1981, 103, 3049.
11. West, R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 2, p 365.
12. West, R. In Comprehensive Organometallics Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 2, p 77.
13. Hengge, E.; Janoschek, R. Chem. Rev. 1995, 95, 1495.
14. Allen, F. H.; Kennard, O. Chem. Des. Autom. News 1993, 8, 31.
15. Carrell, H. L.; Donohue, J. J. Acta Crystallogr. 1972, B28, 1566.
16. Kumar, K.; Litt, M. H.; Chadha, R. K.; Drake, J. E. Can. J. Chem. 1987, 65, 437.
17. Eibl, M.; Katzenbeisser, U.; Hengge, E. J. Organomet. Chem. 1993, 444, 29.
18. Kyushin, S.; Yamaguchi, H.; Okayasu, T.; Yagihashi, Y.; Matsumoto, H.; Goto, M. Chem. Lett. 1994, 221.
19. Throughout this article, the terms boat and boatlike conformations are used to refer to a ring structure with a Cremer and Pople puckering parameter θ close to 90°.
20. One of the referees informed us that the structure of cis-1,4-diphenyldecamethylcyclohexasilane, which also possesses a boat-type ring geometry, was presented by Kleewein, Fischer, and Stüger at the 33rd American Organosilicon meeting in Saginaw in 2000. Hitherto this work has not been published.
21. van Walree, C. A.; Kaats-Richters, V. E. M.; Jenneskens, L. W.; Williams, R. M.; van Stokkum, I. H. M. Chem. Phys. Lett. 2002, 355, 65.
22. Hengge, E.; Eibl, M. J. Organomet. Chem. 1992, 428, 335.
23. Wojnowski, W.; Dreczewski, B.; Herman, A.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Angew. Chem. 1985, 97, 978.
24. Spielberger, A.; Gspaltl, P.; Siegl, H.; Hengge, E.; Gruber, K. J. Organomet. Chem. 1995, 499, 241.
25. In the articles cited, nothing is mentioned about the cis- or trans-nature of the isolated products.
26. See the NMR Spectroscopy section for the identification of isomers 4a and 4b.
27. Sakurai, H.; Murakami, M.; Kumada, M. J. Am. Chem. Soc. 1969, 91, 519.
28. Levine, S. G.; Ng, A. S. J. Org. Chem. 1985, 50, 390.
29. Barton, T. J.; Bouljouk, P. In Silicon-Based Polymer Science; Zeigler, J. M., Fearon, F. W. G., Eds.; American Chemical Society: Washington, DC, 1990; Vol. 224, p 3.
30. Holmes, R. R. Chem. Rev. 1990, 90, 17.
31. Cremer, D.; Pople, J. A. J. Am. Chem. Soc. 1975, 97, 1354.
32. Evans, D. G.; Boeyens, J. C. A. Acta Crystallogr. 1989, B45, 581.
33. Leong, M. K.; Mastryukov, V. S.; Boggs, J. E. J. Phys. Chem. 1994, 98, 6961.
34. Casarini, N.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 1998, 63, 9125.
35. For 1, an atom-numbering system analogous to that of 2 (Figure 2) has been adopted. The silicon atom bearing the pyrenyl substitutent is Si1. In the description of NMR spectra, the standard numbering of pyrenyl hydrogen atoms (H1-H10) is used for both 1 and 2.
36. Due to experimental conditions the signals of the toluene solvent and the pyrenyl groups were subject to line broadening at 230 K, which was however not as strong as that observed for the Si-Me signals. For instance, the widths at half-height of the 0.9 ppm signal were 1.1 and 2.7 Hz at 280 and 230 K, respectively, while those of the pyrenyl H10 signal amounted to 1.1 and 1.7 Hz at these temperatures. The width of the central toluene line near 2.1 ppm was 0.6 Hz at 280 K and 1.0 Hz at 230 K.
37. Smith, Z.; Almenningen, A.; Hengge, E.; Kovar, D. J. Am. Chem. Soc. 1982, 104, 4362.
38. The pyrenyl chemical shifts were assigned with the aid of NMR spectra of linear 1-pyrenyl-substituted oligosilanes: Gelan, J.; Adriaensens, P.; Vanderzande, D.; Declercq, D.; Hermans, E.; De Schryver, F. C. J. Am. Chem. Soc. 1994, 116, 7877.
39. Reynders, P.; Kuhnle, W.; Zachariasse, K. J. Phys. Chem. 1990, 94, 4073.
40. Declercq, D.; Delbeke, P.; De Schryver, F. C.; Van Meervelt, L.; Miller, R. D. J. Am. Chem. Soc. 1993, 115, 5702.
41. Mitter, F. K.; Hengge, E. J. Organomet. Chem. 1987, 332, 47.
42. Chen, S. M.; Katti, A.; Blinka, A.; West, R. Synthesis 1985, 684.
43. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115.
44. Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement; University of Göttingen: Germany, 1997.
45. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: The Netherlands, 2001.