Facile synthesis of the 1,3-disilacyclohexane ring

Chemistry Letters

Volumn , Issue 12, 1996, Pages 1083-1084

  Mizuno, Katsuya ^a   Inamasu, Naoko ^a   Shimizu, Masaki ^a   Hiyama, Tamejiro ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0347627696     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.1083     Document Type: Article

References (22)

1. a) "The Chemistry of Organosilicon Compounds," ed by S. Patai and Z. Rappoport, John Wiley & Sons, Chichester (1989);
2. b) "Organosilicon Chemistry. From Molecules to Materials," ed by N. Auner and J. Weis, VCH, Weinheim (1994);
3. c) S. Pawlenko, "Organosilicon Chemistry," Walter de Gruyter, Berlin (1986).
4. For reviews of carbacyclic silanes, see a) T. J. Barton, in "Comprehensive Organometallic Chemistry. The Synthesis, Reactions and Structures of Organometallic Compounds," ed by G. Wilkinson, F. G. A. Stone, and E. W. Abel, Pergamon Press, Oxford (1982), Vol. 2, p 205;
5. b) B. J. Aylett and A. C. Sullivan, in "Comprehensive Organometallic Chemistry II," ed by E. W. Abel, F. G. A. Stone, and G. Wilkinson, Pergamon Press, Oxford (1995), Vol. 2, p 45;
6. c) M. V. George and R. Balasubramanian, J. Organomel. Chem. Library, 2, 103 (1976);
7. d) G. Fritz, Angew. Chem., Int. Ed. Engl., 26, 1111 (1987);
8. e) Ref. 1c, p 22.
9. a) T. Kinsho, T. Shimizu, T. Ogihara, T. Kaneko, and M. Nakashima, EP 682,031 (1995); Chem. Abstr., 124, 161201k (1996);
10. b) T. Kinsho, T. Shimizu, T. Ogihara, R. Saito, K. Asakura, and M. Nakashima, EP 673,942 (1995); Chem. Abstr., 124, 72665x (1996);
11. c) T. Ogihara, T. Shimizu, T. Kinsho, T. Kaneko, R. Saito, and H. Kurihara, EP650,969, (1995); Chem. Abstr., 123, 270895q (1995).
12. Recent examples; 1,3-disilacyclohexane: S. Mansel, U. Rief, M.-H. Prosenc, R. Kirsten, and H.-H. Brintzinger, J. Organomet. Chem., 512, 225 (1996); 1,4-disilacyclohexane: T. Hoshi, M. Takahashi, and M. Kira, Chem. Lett., 683 (1996).
13. Recent examples; 1,3-disilacyclohexane: S. Mansel, U. Rief, M.-H. Prosenc, R. Kirsten, and H.-H. Brintzinger, J. Organomet. Chem., 512, 225 (1996); 1,4-disilacyclohexane: T. Hoshi, M. Takahashi, and M. Kira, Chem. Lett., 683 (1996).
14. n-Br[R = Me, Ph; n = 3, 4, 5] followed by treatment with butyllithium gave the corresponding monosilacycloalkanes via intramolecular alkylation in moderate yields. See, A. G. Brook and H. W. Kucera, J. Organomet. Chem., 87, 263 (1975).
15. a) A. G. Brook, J. M. Duff, P. F. Jones, and N. R. Davis, J. Am. Chem. Soc., 89, 431 (1967);
16. b) E. J. Corey, D. Seebach, and R. Freedman, J. Am. Chem. Soc., 89, 434 (1967).
17. 3, F(000) = 816, T = 296 K, λ(Mo-Kα) = 0.71069 Å, 2θmax = 50°; Of the 3809 reflections which were collected, 3593 were unique (Rint = 0.029). No decay correction was applied. The data were corrected for Lorentz and polarization effects. The structure was solved by direct method with the program MITHRIL90 and expanded using Fourier technique. The non-hydrogen atoms were refined anisotropically. Hydrogen atoms were included but not refined The final cycle of full-matrix least-squares refinement was based on 2540 observed reflections {I > 3.00σ(I)} and 181 variable parameters and converged with unweighted and weighted agreement factors of R = 0.034 and Rw = 0.038. All calculations were carried out by using the tcXsan program system.
18. a) E. W. Colvin, "Silicon in Organic Synthesis," Butterworths, Boston (1981), p4.;
19. b) M. J. O. Anteunis and R. Dedeyne, Org. Magn. Reson., 9, 127 (1977).
20. 4, etc.) are reported by Seyferth to attack at the Si atom of 7-siladispiro[2.0.2.1 ]heptane. D. Seyferth, J. Organomet. Chem., 100, 237 (1975). See also, M. Ishikawa, K.-I. Nakagawa, and M. Kumada, J. Organomet. Chem., 178, 105 (1979).
21. 4, etc.) are reported by Seyferth to attack at the Si atom of 7-siladispiro[2.0.2.1 ]heptane. D. Seyferth, J. Organomet. Chem., 100, 237 (1975). See also, M. Ishikawa, K.-I. Nakagawa, and M. Kumada, J. Organomet. Chem., 178, 105 (1979).
22. Geometry was fully optimized by ab initia caclulations without imposing any symmetry constraints at the restricted Hartree-Fock level by using gradient optimization techniques and 6-31G * basis set incorporated Mulliken implemented in a CAChe worksystem. Vibrational frequencies were further calculated for this conformer with the same basis set, which unambiguously showed the obtained conformer as a stationary point.