The first 1,2,4-thiadisiletane ring compound: Synthesis from an overcrowded silylene and carbon disulfide

Chemical Communications

Volumn , Issue 2, 1996, Pages 125-126

  Tokitoh, Norihiro ^a   Suzuki, Hiroyuki ^a   Okazaki, Renji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542582270     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960000125     Document Type: Article

References (23)

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2. P. P. Gasper, in Reactive Intermediates, ed. M. Jones, Jr. and R. A. Moss, Wiley, New York, 1978, vol. 1, pp. 229-277; 1981, vol. 2, pp. 335-385; 1985, vol. 3, pp. 333-427. The synthesis of the first isolable silylene was recently reported: M. Denk, R. Lennon, R. K. Hayashi, R. West, A. V. Belyakov, H. P. Verne, A. Haaland, M. Wagner and N. Metzler, J. Am. Chem. Soc., 1994, 116, 2691.
3. P. P. Gasper, in Reactive Intermediates, ed. M. Jones, Jr. and R. A. Moss, Wiley, New York, 1978, vol. 1, pp. 229-277; 1981, vol. 2, pp. 335-385; 1985, vol. 3, pp. 333-427. The synthesis of the first isolable silylene was recently reported: M. Denk, R. Lennon, R. K. Hayashi, R. West, A. V. Belyakov, H. P. Verne, A. Haaland, M. Wagner and N. Metzler, J. Am. Chem. Soc., 1994, 116, 2691.
4. P. P. Gasper, in Reactive Intermediates, ed. M. Jones, Jr. and R. A. Moss, Wiley, New York, 1978, vol. 1, pp. 229-277; 1981, vol. 2, pp. 335-385; 1985, vol. 3, pp. 333-427. The synthesis of the first isolable silylene was recently reported: M. Denk, R. Lennon, R. K. Hayashi, R. West, A. V. Belyakov, H. P. Verne, A. Haaland, M. Wagner and N. Metzler, J. Am. Chem. Soc., 1994, 116, 2691.
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6. W. Ando, M. Fujita, H. Yoshida and A. Sekiguchi, J. Am. Chem. Soc., 1988, 110, 3310; S. Zhang and R. T. Conlin, J. Am. Chem. Soc., 1991, 113, 4272; S. Zhang, P. E. Wagenseller and R. T. Conlin, J. Am. Chem. Soc., 1991, 113, 4278; D. H. Pae, M. Xiao, M. Y. Chiang and P. P. Gasper, J. Am. Chem. Soc., 1991, 113, 1281; P. Boudjouk, E. Black and R. Kumarathasan, Organometallics, 1991, 10, 2095 and references cited therein.
7. W. Ando, M. Fujita, H. Yoshida and A. Sekiguchi, J. Am. Chem. Soc., 1988, 110, 3310; S. Zhang and R. T. Conlin, J. Am. Chem. Soc., 1991, 113, 4272; S. Zhang, P. E. Wagenseller and R. T. Conlin, J. Am. Chem. Soc., 1991, 113, 4278; D. H. Pae, M. Xiao, M. Y. Chiang and P. P. Gasper, J. Am. Chem. Soc., 1991, 113, 1281; P. Boudjouk, E. Black and R. Kumarathasan, Organometallics, 1991, 10, 2095 and references cited therein.
8. W. Ando, M. Fujita, H. Yoshida and A. Sekiguchi, J. Am. Chem. Soc., 1988, 110, 3310; S. Zhang and R. T. Conlin, J. Am. Chem. Soc., 1991, 113, 4272; S. Zhang, P. E. Wagenseller and R. T. Conlin, J. Am. Chem. Soc., 1991, 113, 4278; D. H. Pae, M. Xiao, M. Y. Chiang and P. P. Gasper, J. Am. Chem. Soc., 1991, 113, 1281; P. Boudjouk, E. Black and R. Kumarathasan, Organometallics, 1991, 10, 2095 and references cited therein.
9. W. Ando, M. Fujita, H. Yoshida and A. Sekiguchi, J. Am. Chem. Soc., 1988, 110, 3310; S. Zhang and R. T. Conlin, J. Am. Chem. Soc., 1991, 113, 4272; S. Zhang, P. E. Wagenseller and R. T. Conlin, J. Am. Chem. Soc., 1991, 113, 4278; D. H. Pae, M. Xiao, M. Y. Chiang and P. P. Gasper, J. Am. Chem. Soc., 1991, 113, 1281; P. Boudjouk, E. Black and R. Kumarathasan, Organometallics, 1991, 10, 2095 and references cited therein.
10. M. Weidenbruch, A. Schäfer, K. Peters and H. G. von Schnering, J. Organamet. Chem., 1986, 314, 25; A. Schäfer, M. Weidenbruch, W. Saak and S. Pohl, Angew. Chem., Int. Ed. Engl., 1987, 26, 776.
11. M. Weidenbruch, A. Schäfer, K. Peters and H. G. von Schnering, J. Organamet. Chem., 1986, 314, 25; A. Schäfer, M. Weidenbruch, W. Saak and S. Pohl, Angew. Chem., Int. Ed. Engl., 1987, 26, 776.
12. M. Weidenbruch, B. Brand-Roth, S. Pohl and W. Saak, Angew. Chem., Int. Ed. Engl., 1987, 29, 90.
13. M. Denk, R. K. Hayashi and R. West, J. Chem. Soc., Chem. Commun., 1994, 33.
14. N. Tokitoh, H. Suzuki, R. Okazaki and K. Ogawa, J. Am. Chem. Soc., 1993, 115, 10428; H. Suzuki, N. Tokitoh, R. Okazaki, J. Harada, K. Ogawa and S. Tomoda, Organometallics, 1995, 14, 1016.
15. N. Tokitoh, H. Suzuki, R. Okazaki and K. Ogawa, J. Am. Chem. Soc., 1993, 115, 10428; H. Suzuki, N. Tokitoh, R. Okazaki, J. Harada, K. Ogawa and S. Tomoda, Organometallics, 1995, 14, 1016.
16. A 1,2,3-thiadisiletane derivative has been synthesized by the reaction of a stable disilene with a thioketone: K. Kabeta, D. R. Powell, J. Hanson and R. West, Organometallics, 1991, 10, 827.
17. A. Ricci, A. Degl'Innocenti, M. Fiorenza, P. Dembech, N. Ramadan, G. Seconi and D. R. M. Walton, Tetrahedron Lett., 1985, 26, 1091.
18. c 301.0 (C=Te)] has been reported for the stable telluroketone, 1,1,3,3-tetramethylindanetellone; M. Minoura, T. Kawashima and R. Okazaki, J. Am. Chem. Soc., 1993, 15, 7019.
19. c 301.0 (C=Te)] has been reported for the stable telluroketone, 1,1,3,3-tetramethylindanetellone; M. Minoura, T. Kawashima and R. Okazaki, J. Am. Chem. Soc., 1993, 15, 7019.
20. c 301.0 (C=Te)] has been reported for the stable telluroketone, 1,1,3,3-tetramethylindanetellone; M. Minoura, T. Kawashima and R. Okazaki, J. Am. Chem. Soc., 1993, 15, 7019.
21. P. Jutzi and A. Möhrke, Angew. Chem., Int. Ed. Engl., 1989, 28, 762.
22. 3-2,4,6)Sn:, see: M. Saito, N. Tokitoh and R. Okazaki, Organometallics, 1995, 14, 3620. At this stage, we cannot account for the difference among the reactivities of R(mes)Si: 2 and these heavier congeners toward carbon disulfide.
23. 3-2,4,6)Sn:, see: M. Saito, N. Tokitoh and R. Okazaki, Organometallics, 1995, 14, 3620. At this stage, we cannot account for the difference among the reactivities of R(mes)Si: 2 and these heavier congeners toward carbon disulfide.