The first stable cyclic disilene: Hexakis(trialkylsilyl)tetrasilacyclobutene

Journal of the American Chemical Society

Volumn 118, Issue 42, 1996, Pages 10303-10304

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

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOSILICON DERIVATIVE;

ARTICLE; DRUG STABILITY; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; SPECTROPHOTOMETRY;

EID: 0029906740     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961913p     Document Type: Article

References (30)

1. For reviews, 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, Chapter 17. (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.
2. For reviews, 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, Chapter 17. (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.
3. For reviews, 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, Chapter 17. (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.
4. For reviews, 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, Chapter 17. (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.
5. For reviews, 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, Chapter 17. (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.
6. For reviews, 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, Chapter 17. (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.
7. For reviews, 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, Chapter 17. (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.
8. 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. An interesting cyclic pergermacycloalkene, tetrakis(tri-tert-butylsilyl)trigermacyclopropene, was isolated very recently: Sekiguchi, A.; Yamazaki, H.; Kabuto, C.; Sakurai, H.; Nagase, S. J. Am. Chem. Soc. 1995, 117, 8025.
9. 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. An interesting cyclic pergermacycloalkene, tetrakis(tri-tert-butylsilyl)trigermacyclopropene, was isolated very recently: Sekiguchi, A.; Yamazaki, H.; Kabuto, C.; Sakurai, H.; Nagase, S. J. Am. Chem. Soc. 1995, 117, 8025.
10. 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. An interesting cyclic pergermacycloalkene, tetrakis(tri-tert-butylsilyl)trigermacyclopropene, was isolated very recently: Sekiguchi, A.; Yamazaki, H.; Kabuto, C.; Sakurai, H.; Nagase, S. J. Am. Chem. Soc. 1995, 117, 8025.
11. Woodward. R. B.; Hoffmann, R. The conservation of orbital symintery; Verlag-Chemie: Weinheim, 1970.
12. See also: (a) Spellmeyer, D. C; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 3412. (b) Nguyen, K. A.; Gordon, M. S. J. Am. Chem. Soc. 1995, 117, 3835 and references cited therein, (c) Leigh, W. J.; Postigo, J. A.; Venneri, P. C. J. Am. Chem. Soc: 1995, 117, 7826 and references cited therein.
13. See also: (a) Spellmeyer, D. C; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 3412. (b) Nguyen, K. A.; Gordon, M. S. J. Am. Chem. Soc. 1995, 117, 3835 and references cited therein, (c) Leigh, W. J.; Postigo, J. A.; Venneri, P. C. J. Am. Chem. Soc: 1995, 117, 7826 and references cited therein.
14. See also: (a) Spellmeyer, D. C; Houk, K. N. J. Am. Chem. Soc. 1988, 110, 3412. (b) Nguyen, K. A.; Gordon, M. S. J. Am. Chem. Soc. 1995, 117, 3835 and references cited therein, (c) Leigh, W. J.; Postigo, J. A.; Venneri, P. C. J. Am. Chem. Soc: 1995, 117, 7826 and references cited therein.
15. -3) 465 (6.81), 359 (1.06), 308 (sh, 4.07), 271 (sh, 10.6).
16. w = 0.0940. All calculations were performed by an ACOS-3900 computer at Tohoku University with the applied library program UNICS III system and RANTAN81 program.
17. Kira, M.; Maruyama, T.; Kabuto, C.; Ebata, K.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1489.
18. 9
19. (a) Jones, R.; Williams, D. J.; Kabe, Y.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1986, 25, 173.
20. (b) Masamune, S.; Kabe, Y.; Collins, S.; Williams, D. J.; Jones, R. J. Am. Chem. Soc. 1987, 107, 5552.
21. (c) Kawase, T.; Batcheller, S. A.; Masamune, S. Chem. Lett. 1987, 227.
22. (a) Schleyer, P. v. R.; Sax, A. F.; Kalcher, J.; Janoschek, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 364.
23. (b) Schoeller, W. W.; Dabisch, T.; Busch, T. Inorg. Chem. 1987, 26, 4383.
24. (c) Nagase, S.; Kudo, T. J. Chem. Soc., Chem. Commun. 1988, 54.
25. (d) Kudo, T.; Nagase, S. J. Phys. Chem. 1992, 96, 9189.
26. (e) Boatz, J. A.; Gordon, M. S. J. Phys. Chem. 1989, 93, 2888.
27. (f) Boatz, J. A.; Gordon, M. S. Organometallics 1996, 15, 2118.
28. 2), 4.1, 5.2, 6.1, 6.3, 7.6, 9.1, 18.9 (SiOH).
29. w = 0.071. The X-ray analysis revealed a disordered structure which had an approximate, noncrystallographic, 2-fold axis normal to the plane of the cyclotetrasilane ring. The disorder is confined to the axial hydroxy group which has 37 and 63% site occupancies on Si(1) and Si(3), respectively. All calculations were performed using the TEXSAN crystallographic software package of Molecular Structure Coorporation.
30. 6 isomers have shown that tetrasilabicyclo[1.1.0]butane is more stable than tetrasilacyclobutene with the small energy difference of 3.4 kcal/mol: Boatz, J. A.; Gordon, M. S. J. Phys. Chem. 1988, 92, 3037.