Molecular structure of fluorenyllithium

Organometallics

Volumn 17, Issue 16, 1998, Pages 3512-3515

  Üffing, Christoph ^a   Köppe, Ralf ^a   Schnöckel, Hansgeorg ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000189007     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980103e     Document Type: Article

References (30)

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12. + ions form additional inter- or intramolecular Li - arene interactions. Though these interactions with respect to the distances are similar to those in the species described here, the former ones should not be discussed here because a separation of different interactions at the same Li atom - similar to the above-mentioned donor-stabilized arene complexes - is not possible: (a) Ruhlandt-Senge, K.; Ellison, J. J.; Wehmschulte, R. J.; Pauer, F.; Power, P. P. J. Am. Chem. Soc. 1993, 115, 11353-11357. (b) Schiemenz, B.; Power, P. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2150-2151. (c) Gemünd, B.; Nöth, H.; Sachdev, H.; Schmidt, M. Chem. Ber. 1996, 129, 1335-1344.
13. + ions form additional inter- or intramolecular Li - arene interactions. Though these interactions with respect to the distances are similar to those in the species described here, the former ones should not be discussed here because a separation of different interactions at the same Li atom - similar to the above-mentioned donor-stabilized arene complexes - is not possible: (a) Ruhlandt-Senge, K.; Ellison, J. J.; Wehmschulte, R. J.; Pauer, F.; Power, P. P. J. Am. Chem. Soc. 1993, 115, 11353-11357. (b) Schiemenz, B.; Power, P. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2150-2151. (c) Gemünd, B.; Nöth, H.; Sachdev, H.; Schmidt, M. Chem. Ber. 1996, 129, 1335-1344.
14. + ions form additional inter- or intramolecular Li - arene interactions. Though these interactions with respect to the distances are similar to those in the species described here, the former ones should not be discussed here because a separation of different interactions at the same Li atom - similar to the above-mentioned donor-stabilized arene complexes - is not possible: (a) Ruhlandt-Senge, K.; Ellison, J. J.; Wehmschulte, R. J.; Pauer, F.; Power, P. P. J. Am. Chem. Soc. 1993, 115, 11353-11357. (b) Schiemenz, B.; Power, P. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2150-2151. (c) Gemünd, B.; Nöth, H.; Sachdev, H.; Schmidt, M. Chem. Ber. 1996, 129, 1335-1344.
15. (a) Jemmis, E. D.; Schleyer, P. v. R. J. Am. Chem. Soc. 1982, 104, 4781-4788.
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19. (a) Zargel, F.; Gallucci, J. C.; Meunier, P.; Gautheron, B.; Sivik, M. R.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 6466-6467.
20. Crystals of [7bH-indeno[1,2,3:j,k]fluorenyllithium contain half a molecule of benzene per formula unit: (a) Bladauski, D.; Dietrich, H.; Hecht, H.-J.; Rewicki, D. Angew. Chem., Int. Ed. Engl. 1977, 16, 474. (b) Bladauski, D.; Broser, W.; Hecht, H.-J.; Rewicki, D.; Dietrich, H. Chem. Ber. 1979, 112, 1380-1391.
21. Crystals of [7bH-indeno[1,2,3:j,k]fluorenyllithium contain half a molecule of benzene per formula unit: (a) Bladauski, D.; Dietrich, H.; Hecht, H.-J.; Rewicki, D. Angew. Chem., Int. Ed. Engl. 1977, 16, 474. (b) Bladauski, D.; Broser, W.; Hecht, H.-J.; Rewicki, D.; Dietrich, H. Chem. Ber. 1979, 112, 1380-1391.
22. After this paper had been accepted for publication, we became aware of a preliminary description of the structure of lithium fluorenide, which was not included in the Cambridge Data File, though this short publication is 15 years old: Schmidt, H.-J.; Rewicki, D. Acta Crystallogr. 1984, A40, C293. A transformation of coordinates of the cell dimensions presented in this former paper shows that this structure is in principle identical with that discussed in the present paper.
23. Investigations of more soluble fluorenyllithium compounds such as [9-(2-hexyl)fluorenyl]lithium gave evidence of dimeric units, for which on the basis of Li NMR data (high-field-shifted signals) a sandwich-like structure has been postulated: (a) Exner, M. M.; Waack, R.; Steiner, E. C. J. Am. Chem. Soc. 1973, 95, 7009-7018. (b) Takaki, U.; Collins, G. L.; Smid, J. J. Organomet. Chem. 1978, 145, 139-149.
24. Investigations of more soluble fluorenyllithium compounds such as [9-(2-hexyl)fluorenyl]lithium gave evidence of dimeric units, for which on the basis of Li NMR data (high-field-shifted signals) a sandwich-like structure has been postulated: (a) Exner, M. M.; Waack, R.; Steiner, E. C. J. Am. Chem. Soc. 1973, 95, 7009-7018. (b) Takaki, U.; Collins, G. L.; Smid, J. J. Organomet. Chem. 1978, 145, 139-149.
25. - the shorter distance between the ring planes in 1 is based on reduced electrostatic repulsion while the longer Li - C distance in 1 is attributed to the larger size of a six-membered-ring system in contrast to a five-membered one.
26. (a) Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467-473.
27. (b) Sheldrick, G. M. Universität Göttingen, 1993.
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