Reactions of a silanediyl with carbon-oxygen and carbon-nitrogen double bonds

Journal of Organic Chemistry

Volumn 61, Issue 10, 1996, Pages 3315-3319

  Belzner, Johannes ^a   Ihmels, Heiko ^a   Pauletto, Lara ^a   Noltemeyer, Matthias ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006298183     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951583b     Document Type: Article

References (23)

1. Ando, W.; Ikeno, M.; Sekiguchi, A. J. Am. Chem. Soc. 1977, 99, 6447-6449.
2. Ando, W.; Hamada, Y.; Sekiguchi, A. Tetrahedron Lett. 1982, 23, 5323-5326.
3. Ando, W.; Hagiwara, K.; Sekiguchi, A. Organometallics 1987, 6, 2270-2271.
4. Moss, R. A ; Jones, M. Jr. In Reactive Intermediates; Jones, M., Jr., Moss, R. A., Eds.; Wiley: New York, 1985; Vol. 3, pp 45-108 and related references cited therein.
5. Belzner, J.; Ihmels, H.; Kneisel, B. O.; Gould, R. O.; Herbst-Irmer, R. Organometallics 1995, 14, 305-311
6. Belzner, J.; Ihmels, H Tetrahedron Lett. 1993, 34, 6541-6544.
7. Belzner, J.; Ihmels, H ; Kneisel, B. O.; Herbst-Irmer, R. J. Chem. Soc., Chem. Commun. 1994, 1989-1990
8. Belzner, J. J. Organomet. Chem. 1992, 430, C51-C55.
9. Lappert, M. F.; Misra, M. C.; Onyszchuk, M.; Rowe, R. S.; Power, P. P.; Slade, M. J. J. Organomet. Chem. 1987, 330, 31-46.
10. Kinetic investigations show that the reactions of 1 with substituted styrenes and alkynes are favored by electron-withdrawing substituents, i.e., the rate-determining step of the addition of silanediyl 2 to the multiple bond is of nucleophilic character: Belzner, J.; Ihmels, H.; Dehnert, U. Unpublished results.
11. Belzner, J.; Schar, D.; Kneisel, B. O.; Herbst-Irmer, R. Organometallics 1995, 14, 1840-1843.
12. Details of X-ray structure determination as well as tables of atomic coordinates, bond lengths and angles, anisotropic displacement parameters, and hydrogen atom coordinates of compounds 14 and 42a have been deposited with the Cambridge Crystallographic Data Centre. These data may be obtained, upon request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
13. Ando, W.; Ikeno, M.; Sekiguchi, A. J. Am. Chem. Soc. 1978, 100, 3613-3615.
14. See, e.g.: de March, P.; Huisgen, R. J. Am. Chem. Soc. 1982, 104, 4592-4952.
15. Another mechanistic pathway from 1 to 16 via radical intermediates cannot be excluded, but seems less probable.
16. Ando, W.; Hamada, Y.; Sekiguchi, A. J. Chem. Soc., Chem. Commun. 1983, 952-954.
17. See, e.g : Williams, E. A. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1989; pp 511-554.
18. Weidenbruch, M.; Piel, H.; Peters, K.; von Schnering, H. G. Organometallics 1993, 12, 2881-2882.
19. 20 for another diazasilacyclopentene.
20. Weidenbruch, M.; Lesch, A.; Peters, K. J. Organomet. Chem. 1991, 407, 31-40.
21. See ref 5 and references cited therein.
22. Reddelien, G. Chem. Ber. 1913, 46, 2718-2723.
23. Kliegman, J. M.; Barnes, R. K. Tetrahedron 1970, 26, 2555-2560.