An unexpected reaction of silacyclopropene to form an organodilithiosilane: Isolation and characterization of a 1,1-dilithiosilane derivative [11]

Journal of the American Chemical Society

Volumn 121, Issue 43, 1999, Pages 10231-10232

  Sekiguchi, Akira ^a   Ichinohe, Masaaki ^a   Yamaguchi, Shoji ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; SILANE DERIVATIVE;

CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; LETTER;

EID: 0033520795     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991694i     Document Type: Letter

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18. For silyl-substituted ethylenes and their alkali metal derivatives, see: (a) Sekiguchi, A.; Nakanishi, T.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1989, 111, 3748. (b) Sekiguchi, A.; Ichinohe, M.; Kabuto, C.; Sakurai, H. Organometallics 1995, 14, 1092. (c) Sekiguchi, A.; Ichinohe, M.; Takahashi, M.; Kabuto, C.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1533. For silyl-substituted benzenes and their alkali metal derivatives, see: (d) Sakurai, H.; Ebata, K.; Kabuto, C.; Sekiguchi, A. J. Am. Chem. Soc. 1990, 112, 1799. (e) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 1464. (f) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 7081. For other silyl-substituted π-electron compounds and their alkali metal derivatives, see: (g) Sekiguchi, A.; Sugai, Y.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1993, 115, 1144. (h) Sekiguchi, A.; Matsuo, T.; Kabuto, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2462. (i) Sekiguchi, A.; Matsuo, T.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1662. (j) Matsuo, T.; Sekiguchi, A.; Ichinohe, M.; Ebata, K.; Sakurai, H. Organometallics 1998, 17, 3143.
19. For silyl-substituted ethylenes and their alkali metal derivatives, see: (a) Sekiguchi, A.; Nakanishi, T.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1989, 111, 3748. (b) Sekiguchi, A.; Ichinohe, M.; Kabuto, C.; Sakurai, H. Organometallics 1995, 14, 1092. (c) Sekiguchi, A.; Ichinohe, M.; Takahashi, M.; Kabuto, C.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1533. For silyl-substituted benzenes and their alkali metal derivatives, see: (d) Sakurai, H.; Ebata, K.; Kabuto, C.; Sekiguchi, A. J. Am. Chem. Soc. 1990, 112, 1799. (e) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 1464. (f) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 7081. For other silyl-substituted π-electron compounds and their alkali metal derivatives, see: (g) Sekiguchi, A.; Sugai, Y.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1993, 115, 1144. (h) Sekiguchi, A.; Matsuo, T.; Kabuto, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2462. (i) Sekiguchi, A.; Matsuo, T.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1662. (j) Matsuo, T.; Sekiguchi, A.; Ichinohe, M.; Ebata, K.; Sakurai, H. Organometallics 1998, 17, 3143.
20. For silyl-substituted ethylenes and their alkali metal derivatives, see: (a) Sekiguchi, A.; Nakanishi, T.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1989, 111, 3748. (b) Sekiguchi, A.; Ichinohe, M.; Kabuto, C.; Sakurai, H. Organometallics 1995, 14, 1092. (c) Sekiguchi, A.; Ichinohe, M.; Takahashi, M.; Kabuto, C.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1533. For silyl-substituted benzenes and their alkali metal derivatives, see: (d) Sakurai, H.; Ebata, K.; Kabuto, C.; Sekiguchi, A. J. Am. Chem. Soc. 1990, 112, 1799. (e) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 1464. (f) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 7081. For other silyl-substituted π-electron compounds and their alkali metal derivatives, see: (g) Sekiguchi, A.; Sugai, Y.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1993, 115, 1144. (h) Sekiguchi, A.; Matsuo, T.; Kabuto, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2462. (i) Sekiguchi, A.; Matsuo, T.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1662. (j) Matsuo, T.; Sekiguchi, A.; Ichinohe, M.; Ebata, K.; Sakurai, H. Organometallics 1998, 17, 3143.
21. For silyl-substituted ethylenes and their alkali metal derivatives, see: (a) Sekiguchi, A.; Nakanishi, T.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1989, 111, 3748. (b) Sekiguchi, A.; Ichinohe, M.; Kabuto, C.; Sakurai, H. Organometallics 1995, 14, 1092. (c) Sekiguchi, A.; Ichinohe, M.; Takahashi, M.; Kabuto, C.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1533. For silyl-substituted benzenes and their alkali metal derivatives, see: (d) Sakurai, H.; Ebata, K.; Kabuto, C.; Sekiguchi, A. J. Am. Chem. Soc. 1990, 112, 1799. (e) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 1464. (f) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 7081. For other silyl-substituted π-electron compounds and their alkali metal derivatives, see: (g) Sekiguchi, A.; Sugai, Y.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1993, 115, 1144. (h) Sekiguchi, A.; Matsuo, T.; Kabuto, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2462. (i) Sekiguchi, A.; Matsuo, T.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1662. (j) Matsuo, T.; Sekiguchi, A.; Ichinohe, M.; Ebata, K.; Sakurai, H. Organometallics 1998, 17, 3143.
22. For silyl-substituted ethylenes and their alkali metal derivatives, see: (a) Sekiguchi, A.; Nakanishi, T.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1989, 111, 3748. (b) Sekiguchi, A.; Ichinohe, M.; Kabuto, C.; Sakurai, H. Organometallics 1995, 14, 1092. (c) Sekiguchi, A.; Ichinohe, M.; Takahashi, M.; Kabuto, C.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1533. For silyl-substituted benzenes and their alkali metal derivatives, see: (d) Sakurai, H.; Ebata, K.; Kabuto, C.; Sekiguchi, A. J. Am. Chem. Soc. 1990, 112, 1799. (e) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 1464. (f) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 7081. For other silyl-substituted π-electron compounds and their alkali metal derivatives, see: (g) Sekiguchi, A.; Sugai, Y.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1993, 115, 1144. (h) Sekiguchi, A.; Matsuo, T.; Kabuto, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2462. (i) Sekiguchi, A.; Matsuo, T.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1662. (j) Matsuo, T.; Sekiguchi, A.; Ichinohe, M.; Ebata, K.; Sakurai, H. Organometallics 1998, 17, 3143.
23. For silyl-substituted ethylenes and their alkali metal derivatives, see: (a) Sekiguchi, A.; Nakanishi, T.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1989, 111, 3748. (b) Sekiguchi, A.; Ichinohe, M.; Kabuto, C.; Sakurai, H. Organometallics 1995, 14, 1092. (c) Sekiguchi, A.; Ichinohe, M.; Takahashi, M.; Kabuto, C.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1533. For silyl-substituted benzenes and their alkali metal derivatives, see: (d) Sakurai, H.; Ebata, K.; Kabuto, C.; Sekiguchi, A. J. Am. Chem. Soc. 1990, 112, 1799. (e) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 1464. (f) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 7081. For other silyl-substituted π-electron compounds and their alkali metal derivatives, see: (g) Sekiguchi, A.; Sugai, Y.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1993, 115, 1144. (h) Sekiguchi, A.; Matsuo, T.; Kabuto, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2462. (i) Sekiguchi, A.; Matsuo, T.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1662. (j) Matsuo, T.; Sekiguchi, A.; Ichinohe, M.; Ebata, K.; Sakurai, H. Organometallics 1998, 17, 3143.
24. For silyl-substituted ethylenes and their alkali metal derivatives, see: (a) Sekiguchi, A.; Nakanishi, T.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1989, 111, 3748. (b) Sekiguchi, A.; Ichinohe, M.; Kabuto, C.; Sakurai, H. Organometallics 1995, 14, 1092. (c) Sekiguchi, A.; Ichinohe, M.; Takahashi, M.; Kabuto, C.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1533. For silyl-substituted benzenes and their alkali metal derivatives, see: (d) Sakurai, H.; Ebata, K.; Kabuto, C.; Sekiguchi, A. J. Am. Chem. Soc. 1990, 112, 1799. (e) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 1464. (f) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 7081. For other silyl-substituted π-electron compounds and their alkali metal derivatives, see: (g) Sekiguchi, A.; Sugai, Y.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1993, 115, 1144. (h) Sekiguchi, A.; Matsuo, T.; Kabuto, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2462. (i) Sekiguchi, A.; Matsuo, T.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1662. (j) Matsuo, T.; Sekiguchi, A.; Ichinohe, M.; Ebata, K.; Sakurai, H. Organometallics 1998, 17, 3143.
25. For silyl-substituted ethylenes and their alkali metal derivatives, see: (a) Sekiguchi, A.; Nakanishi, T.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1989, 111, 3748. (b) Sekiguchi, A.; Ichinohe, M.; Kabuto, C.; Sakurai, H. Organometallics 1995, 14, 1092. (c) Sekiguchi, A.; Ichinohe, M.; Takahashi, M.; Kabuto, C.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1533. For silyl-substituted benzenes and their alkali metal derivatives, see: (d) Sakurai, H.; Ebata, K.; Kabuto, C.; Sekiguchi, A. J. Am. Chem. Soc. 1990, 112, 1799. (e) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 1464. (f) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 7081. For other silyl-substituted π-electron compounds and their alkali metal derivatives, see: (g) Sekiguchi, A.; Sugai, Y.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1993, 115, 1144. (h) Sekiguchi, A.; Matsuo, T.; Kabuto, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2462. (i) Sekiguchi, A.; Matsuo, T.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1662. (j) Matsuo, T.; Sekiguchi, A.; Ichinohe, M.; Ebata, K.; Sakurai, H. Organometallics 1998, 17, 3143.
26. For silyl-substituted ethylenes and their alkali metal derivatives, see: (a) Sekiguchi, A.; Nakanishi, T.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1989, 111, 3748. (b) Sekiguchi, A.; Ichinohe, M.; Kabuto, C.; Sakurai, H. Organometallics 1995, 14, 1092. (c) Sekiguchi, A.; Ichinohe, M.; Takahashi, M.; Kabuto, C.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1533. For silyl-substituted benzenes and their alkali metal derivatives, see: (d) Sakurai, H.; Ebata, K.; Kabuto, C.; Sekiguchi, A. J. Am. Chem. Soc. 1990, 112, 1799. (e) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 1464. (f) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 7081. For other silyl-substituted π-electron compounds and their alkali metal derivatives, see: (g) Sekiguchi, A.; Sugai, Y.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1993, 115, 1144. (h) Sekiguchi, A.; Matsuo, T.; Kabuto, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2462. (i) Sekiguchi, A.; Matsuo, T.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1662. (j) Matsuo, T.; Sekiguchi, A.; Ichinohe, M.; Ebata, K.; Sakurai, H. Organometallics 1998, 17, 3143.
27. 2] (Tbt = 2,4,6-tris-[bis(trimethylsilyl)methyl]phenyl, Dip = 2,6-diisopropylphenyl), by the reaction of the corresponding dibromosilane with a 5 equimolar amount of lithium naphthalenide (LiNp) in THF at -78°C. However, no spectroscopic and crystallographic characterization of the dilithiosilane has been given; see: Tokitoh, N.; Hatano, K.; Sadahiro, T.; Okazaki, R. Chem Lett 1999, 931.
28. 2Hg with lithium metal in hydrocarbon solvent. We thank Prof. Y. Apeloig for informing us prior to publication.
29. 5: C. 60.85; H, 11.78. Found: C, 60.80; H, 11.95.
30. 2Si) with a 4 equimolar amount of LiNp in THF at -78°C.
31. + - 43, 0.8), 56 (100).
32. Conlin, R. T.; Gaspar, P. P. J. Am. Chem. Soc. 1976, 98, 3715.
33. -3, temperature 120 K, R = 0.086, Rw = 0.164, 5019 reflections (I > 3σ(I)), 388 parameters.
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39. 8, 200 K, δ) 2.18.
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