Synthesis and characterization of a cyclobutadiene dianion dilithium salt: Evidence for aromaticity [9]

Journal of the American Chemical Society

Volumn 122, Issue 23, 2000, Pages 5652-5653

  Sekiguchi, Akira ^a   Matsuo, Tsukasa ^a   Watanabe, Hidetoshi ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BENZENE DERIVATIVE; CYCLOBUTANE DERIVATIVE; ESTER DERIVATIVE; ETHYLENE DERIVATIVE; LITHIUM SALT;

CHEMICAL STRUCTURE; CRYSTALLIZATION; ION EXCHANGE CHROMATOGRAPHY; LETTER; MOLECULAR STABILITY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0034647228     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0004175     Document Type: Letter

References (26)

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12. For silyl-substituted ethylene dianion dilithium 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. Sekiguchi, A.; Ichinohe, M.; Takahashi, M.; Kabuto, C.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1533.
13. For silyl-substituted ethylene dianion dilithium 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. Sekiguchi, A.; Ichinohe, M.; Takahashi, M.; Kabuto, C.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1533.
14. For silyl-substituted ethylene dianion dilithium 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. Sekiguchi, A.; Ichinohe, M.; Takahashi, M.; Kabuto, C.; Sakurai, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1533.
15. For silyl-substituted benzene dianion dilithium derivatives, see: (a) Sekiguchi, A.: Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 1464. (b) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 7081. Ebata, K.; Selaka, W.; Inoue, T.; Kabuto, C.; Kira, M.; Sakurai, H. J. Am. Chem. Soc. 1998, 120, 1335.
16. For silyl-substituted benzene dianion dilithium derivatives, see: (a) Sekiguchi, A.: Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 1464. (b) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 7081. Ebata, K.; Selaka, W.; Inoue, T.; Kabuto, C.; Kira, M.; Sakurai, H. J. Am. Chem. Soc. 1998, 120, 1335.
17. For silyl-substituted benzene dianion dilithium derivatives, see: (a) Sekiguchi, A.: Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 1464. (b) Sekiguchi, A.; Ebata, K.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1991, 113, 7081. Ebata, K.; Selaka, W.; Inoue, T.; Kabuto, C.; Kira, M.; Sakurai, H. J. Am. Chem. Soc. 1998, 120, 1335.
18. 2 with bis(trimethylsilyl)acetylene, see: Fritch, J. R.; Vollhardt, K. P. C.; Thompson, M. R.; Day, V. W. J. Am. Chem. Soc. 1979, 101, 2768.
19. 8) δ -5.07.
20. 4 (R = H, Me, t-Bu). We thank professor Schleyer for informing us of this recent paper.
21. - complexed to ring faces as an aromaticity probe has been reported, see ref 7b. (a) Paquette, L. A.; Bauer, W.; Sivik, M. R.; Bühl, M.; Feigel, M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 8776. (b) Jiao, H.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1760.
22. - complexed to ring faces as an aromaticity probe has been reported, see ref 7b. (a) Paquette, L. A.; Bauer, W.; Sivik, M. R.; Bühl, M.; Feigel, M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1990, 112, 8776. (b) Jiao, H.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1760.
23. 2) appearing at δ 10.7 as an antiaromatic system has been reported (ref 9b).
24. 2) appearing at δ 10.7 as an antiaromatic system has been reported (ref 9b).
25. 8) δ -5.01.
26. w = 0.1646 for all data). GOF = 1.026.