The first stable cyclotrisilene [16]

Journal of the American Chemical Society

Volumn 121, Issue 4, 1999, Pages 886-887

  Iwamoto, Takeaki ^a   Kabuto, Chizuko ^a   Kira, Mitsuo ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOTRISILENE DERIVATIVE; PERMETALLACYCLOALKENE; UNCLASSIFIED DRUG;

CHEMICAL BINDING; CHEMICAL REACTION KINETICS; LETTER; METAL BINDING; ORGANIC CHEMISTRY; REDUCTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033518567     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983623+     Document Type: Letter

References (36)

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2. 2 (M = Si, Ge, and Sn), see: (a) West, R. Pure Appl. Chem. 1984, 56, 163. (b) Raabe, G.; Michl, J. Chem. Rev. 1985, 85, 419. (c) West, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 1201. (d) Raabe, G.; Michl, J. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: New York, 1989; Part 2. (e) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283. (f) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902. (g) Grev, R. S. Adv. Organomet. Chem. 1991, 33, 125. (h) Okazaki, R.; West, R. Adv. Organomet. Chem., 1996, 39, 231.
3. 2 (M = Si, Ge, and Sn), see: (a) West, R. Pure Appl. Chem. 1984, 56, 163. (b) Raabe, G.; Michl, J. Chem. Rev. 1985, 85, 419. (c) West, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 1201. (d) Raabe, G.; Michl, J. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: New York, 1989; Part 2. (e) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283. (f) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902. (g) Grev, R. S. Adv. Organomet. Chem. 1991, 33, 125. (h) Okazaki, R.; West, R. Adv. Organomet. Chem., 1996, 39, 231.
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11. Very recently, Wiberg et al. reported that the novel cyclotetrasilene, 1,2,3,4-tetrakis(tri-tert-butylsilyl)-1,2-diiodo-3,4-cyclotetrasilene, was obtained by a simple reaction of tetrakis(tri-tert-butylsilyl)tetrahedrane with iodine. Wiberg, N.; Auer, H.; Nöth, H.; Knizek J.; Polborn K. Angew. Chem., Int. Ed. Engl. 1998, 36, 2869.
12. The formation of a Dewar hexasilabenzene by the photolysis of the corresponding hexasilaprismane was evidenced spectroscopically: (a) Sekiguchi, A.; Yatabe, T.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1993, 115, 5853. (b) Sekiguchi, A.; Yatabe, T.; Doi, S.; Sakurai, H. Phosphorus, Sulfur, Silicon Relat. Elem. 1994, 93/94, 193.
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15. Cyclotrigermenes: (a) Sekiguchi, A.; Yamazaki, H.; Kabuto, C.; Sakurai, H.; Nagase, S. J. Am. Chem. Soc. 1995, 117, 8025. Cyclotrigermenium ions: (b) Sekiguchi, A.; Tsukamoto, M.; Ichinohe, M. Science 1997, 275, 60. (c) Sekiguchi, A.; Tsukamoto, M.; Ichinohe, M.; Fukaya, N. Phosphorous, Sulfur, Silicon Relat. Elem. 1997, 124 and 125, 323. (d) Ichinohe, M.; Fukaya, N.; Sekiguchi, A. Chem. Lett. 1998, 1045.
16. Cyclotrigermenes: (a) Sekiguchi, A.; Yamazaki, H.; Kabuto, C.; Sakurai, H.; Nagase, S. J. Am. Chem. Soc. 1995, 117, 8025. Cyclotrigermenium ions: (b) Sekiguchi, A.; Tsukamoto, M.; Ichinohe, M. Science 1997, 275, 60. (c) Sekiguchi, A.; Tsukamoto, M.; Ichinohe, M.; Fukaya, N. Phosphorous, Sulfur, Silicon Relat. Elem. 1997, 124 and 125, 323. (d) Ichinohe, M.; Fukaya, N.; Sekiguchi, A. Chem. Lett. 1998, 1045.
17. Cyclotrigermenes: (a) Sekiguchi, A.; Yamazaki, H.; Kabuto, C.; Sakurai, H.; Nagase, S. J. Am. Chem. Soc. 1995, 117, 8025. Cyclotrigermenium ions: (b) Sekiguchi, A.; Tsukamoto, M.; Ichinohe, M. Science 1997, 275, 60. (c) Sekiguchi, A.; Tsukamoto, M.; Ichinohe, M.; Fukaya, N. Phosphorous, Sulfur, Silicon Relat. Elem. 1997, 124 and 125, 323. (d) Ichinohe, M.; Fukaya, N.; Sekiguchi, A. Chem. Lett. 1998, 1045.
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21. max/nm (ε) 482 (2640), 401 (1340), 315 (sh, 7690), 245 (sh, 3670), 217 (5210).
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24. 12 +103.1, and +187.8, respectively. (Formula Presented)
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26. u) for ethylene, cyclopropene, and cyclobutene are reported to be 123.5, 108.7, and 137.2 ppm, respectively. (a) Kalinowski, H.-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; John Wiley & Sons: New York, 1988. See also for cyclopropene: (b) Günther, H.; Seel, H. Org. Magn. Reson. 1976, 8, 299. For cyclobutene: (c) Dorman, D. E.; Jautelat, M.; Roberts, J. D. J. Org. Chem. 1971, 36, 2757. For ethylene: Savitsky, G. B.; Ellis, P. D.; Namikawa, K.; Maciel, G. E. J. Chem. Phys. 1968, 49, 2395.
27. u) for ethylene, cyclopropene, and cyclobutene are reported to be 123.5, 108.7, and 137.2 ppm, respectively. (a) Kalinowski, H.-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; John Wiley & Sons: New York, 1988. See also for cyclopropene: (b) Günther, H.; Seel, H. Org. Magn. Reson. 1976, 8, 299. For cyclobutene: (c) Dorman, D. E.; Jautelat, M.; Roberts, J. D. J. Org. Chem. 1971, 36, 2757. For ethylene: Savitsky, G. B.; Ellis, P. D.; Namikawa, K.; Maciel, G. E. J. Chem. Phys. 1968, 49, 2395.
28. u) for ethylene, cyclopropene, and cyclobutene are reported to be 123.5, 108.7, and 137.2 ppm, respectively. (a) Kalinowski, H.-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; John Wiley & Sons: New York, 1988. See also for cyclopropene: (b) Günther, H.; Seel, H. Org. Magn. Reson. 1976, 8, 299. For cyclobutene: (c) Dorman, D. E.; Jautelat, M.; Roberts, J. D. J. Org. Chem. 1971, 36, 2757. For ethylene: Savitsky, G. B.; Ellis, P. D.; Namikawa, K.; Maciel, G. E. J. Chem. Phys. 1968, 49, 2395.
29. u) for ethylene, cyclopropene, and cyclobutene are reported to be 123.5, 108.7, and 137.2 ppm, respectively. (a) Kalinowski, H.-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; John Wiley & Sons: New York, 1988. See also for cyclopropene: (b) Günther, H.; Seel, H. Org. Magn. Reson. 1976, 8, 299. For cyclobutene: (c) Dorman, D. E.; Jautelat, M.; Roberts, J. D. J. Org. Chem. 1971, 36, 2757. For ethylene: Savitsky, G. B.; Ellis, P. D.; Namikawa, K.; Maciel, G. E. J. Chem. Phys. 1968, 49, 2395.
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31. 2Si).
32. 19 R = 0. 049 (data with I > 2σ(I)), Rw = 0.159 (all data).
33. A mechanistic study of the reactions of disilenes and haloalkanes is under way. Trans arrangement of two chlorine atoms in 5 can be explained by a stepwise chlorine abstraction mechanism in the reaction of 5 with carbon tetrachloride.
34. Altomare A.; Burla, M. C.; Camalli, M.; Cascarano G.; Giacovazzo, C.; Guagliardi A. J. Appl. Crystallogr. 1994, 27, 435.
35. Sheldrick, G. M. SHELXL93, Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1993.
36. 3Si, the disilavinylidene isomer is calculated to be 6.2 kcal/mol more stable than the trans-bent disilyne isomer. Kobayashi, K.; Nagase, S. Organometallics 1997, 16, 2489.