Interaction between alkali metal aromatic ketone radical anions and the chlorides of lithium and magnesium in solution. A case of a carbon-carbon bond strengthening through complex formation

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 12, 1999, Pages 2685-2690

  Micha Screttas, Maria ^a   Heropoulos, Georgios A ^a   Steele, Barry R ^a  

^a INSTITUTE OF BIOLOGY   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001657729     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906337d     Document Type: Article

References (41)

1. A. Behrendt, C. G. Screttas, D. Bethell, O. Schiemann and B. R. Steele, J. Chem. Soc., Perkin Trans. 2, 1998, 2039; F. Demol, F. X. Sauvage, A. Devos and M. G. Debacker, Synth. Met., 1999, 99, 155; J. S. Millerand A. J. Epstein, Angew. Chem., 1994, 106, 399; Angew. chem., Int. Ed Engl., 1994, 33, 385; M. Baumgarten and K. Müllen, Top. Curr. Chem. 1994, 169, 1; K. Müllen, Pure Appl. Chem., 1993, 65, 89; U. Müller, M. Adam and K. Müllen, Chem. Ber., 1994, 127, 437; S. H. Yang, C. Mitchell, J. E. Jackson and B. Kahr, Mol. Cryst. Liq. Cryst., 1995, 271, A147.
2. A. Behrendt, C. G. Screttas, D. Bethell, O. Schiemann and B. R. Steele, J. Chem. Soc., Perkin Trans. 2, 1998, 2039; F. Demol, F. X. Sauvage, A. Devos and M. G. Debacker, Synth. Met., 1999, 99, 155; J. S. Millerand A. J. Epstein, Angew. Chem., 1994, 106, 399; Angew. chem., Int. Ed Engl., 1994, 33, 385; M. Baumgarten and K. Müllen, Top. Curr. Chem. 1994, 169, 1; K. Müllen, Pure Appl. Chem., 1993, 65, 89; U. Müller, M. Adam and K. Müllen, Chem. Ber., 1994, 127, 437; S. H. Yang, C. Mitchell, J. E. Jackson and B. Kahr, Mol. Cryst. Liq. Cryst., 1995, 271, A147.
3. A. Behrendt, C. G. Screttas, D. Bethell, O. Schiemann and B. R. Steele, J. Chem. Soc., Perkin Trans. 2, 1998, 2039; F. Demol, F. X. Sauvage, A. Devos and M. G. Debacker, Synth. Met., 1999, 99, 155; J. S. Miller A. J. Epstein, Angew. Chem., 1994, 106, 399; Angew. chem., Int. Ed Engl., 1994, 33, 385; M. Baumgarten and K. Müllen, Top. Curr. Chem. 1994, 169, 1; K. Müllen, Pure Appl. Chem., 1993, 65, 89; U. Müller, M. Adam and K. Müllen, Chem. Ber., 1994, 127, 437; S. H. Yang, C. Mitchell, J. E. Jackson and B. Kahr, Mol. Cryst. Liq. Cryst., 1995, 271, A147.
4. A. Behrendt, C. G. Screttas, D. Bethell, O. Schiemann and B. R. Steele, J. Chem. Soc., Perkin Trans. 2, 1998, 2039; F. Demol, F. X. Sauvage, A. Devos and M. G. Debacker, Synth. Met., 1999, 99, 155; J. S. Millerand A. J. Epstein, Angew. Chem., 1994, 106, 399; Angew. chem., Int. Ed Engl., 1994, 33, 385; M. Baumgarten and K. Müllen, Top. Curr. Chem. 1994, 169, 1; K. Müllen, Pure Appl. Chem., 1993, 65, 89; U. Müller, M. Adam and K. Müllen, Chem. Ber., 1994, 127, 437; S. H. Yang, C. Mitchell, J. E. Jackson and B. Kahr, Mol. Cryst. Liq. Cryst., 1995, 271, A147.
5. A. Behrendt, C. G. Screttas, D. Bethell, O. Schiemann and B. R. Steele, J. Chem. Soc., Perkin Trans. 2, 1998, 2039; F. Demol, F. X. Sauvage, A. Devos and M. G. Debacker, Synth. Met., 1999, 99, 155; J. S. Millerand A. J. Epstein, Angew. Chem., 1994, 106, 399; Angew. chem., Int. Ed Engl., 1994, 33, 385; M. Baumgarten and K. Müllen, Top. Curr. Chem. 1994, 169, 1; K. Müllen, Pure Appl. Chem., 1993, 65, 89; U. Müller, M. Adam and K. Müllen, Chem. Ber., 1994, 127, 437; S. H. Yang, C. Mitchell, J. E. Jackson and B. Kahr, Mol. Cryst. Liq. Cryst., 1995, 271, A147.
6. A. Behrendt, C. G. Screttas, D. Bethell, O. Schiemann and B. R. Steele, J. Chem. Soc., Perkin Trans. 2, 1998, 2039; F. Demol, F. X. Sauvage, A. Devos and M. G. Debacker, Synth. Met., 1999, 99, 155; J. S. Millerand A. J. Epstein, Angew. Chem., 1994, 106, 399; Angew. chem., Int. Ed Engl., 1994, 33, 385; M. Baumgarten and K. Müllen, Top. Curr. Chem. 1994, 169, 1; K. Müllen, Pure Appl. Chem., 1993, 65, 89; U. Müller, M. Adam and K. Müllen, Chem. Ber., 1994, 127, 437; S. H. Yang, C. Mitchell, J. E. Jackson and B. Kahr, Mol. Cryst. Liq. Cryst., 1995, 271, A147.
7. A. Behrendt, C. G. Screttas, D. Bethell, O. Schiemann and B. R. Steele, J. Chem. Soc., Perkin Trans. 2, 1998, 2039; F. Demol, F. X. Sauvage, A. Devos and M. G. Debacker, Synth. Met., 1999, 99, 155; J. S. Millerand A. J. Epstein, Angew. Chem., 1994, 106, 399; Angew. chem., Int. Ed Engl., 1994, 33, 385; M. Baumgarten and K. Müllen, Top. Curr. Chem. 1994, 169, 1; K. Müllen, Pure Appl. Chem., 1993, 65, 89; U. Müller, M. Adam and K. Müllen, Chem. Ber., 1994, 127, 437; S. H. Yang, C. Mitchell, J. E. Jackson and B. Kahr, Mol. Cryst. Liq. Cryst., 1995, 271, A147.
8. A. Behrendt, C. G. Screttas, D. Bethell, O. Schiemann and B. R. Steele, J. Chem. Soc., Perkin Trans. 2, 1998, 2039; F. Demol, F. X. Sauvage, A. Devos and M. G. Debacker, Synth. Met., 1999, 99, 155; J. S. Millerand A. J. Epstein, Angew. Chem., 1994, 106, 399; Angew. chem., Int. Ed Engl., 1994, 33, 385; M. Baumgarten and K. Müllen, Top. Curr. Chem. 1994, 169, 1; K. Müllen, Pure Appl. Chem., 1993, 65, 89; U. Müller, M. Adam and K. Müllen, Chem. Ber., 1994, 127, 437; S. H. Yang, C. Mitchell, J. E. Jackson and B. Kahr, Mol. Cryst. Liq. Cryst., 1995, 271, A147.
9. (a) Z. Hou, A. Fujita, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1996, 118, 2503;
10. (b) C. Näther, H. Bock, Z. Havlas and T. Hauck, Organometallics, 1998, 17, 4707; W. Jost, M. Adam. V. Enkelmann and K. Müllen, Angew. Chem., Int. Ed Engl., 1992, 31, 878.
11. (b) C. Näther, H. Bock, Z. Havlas and T. Hauck, Organometallics, 1998, 17, 4707; W. Jost, M. Adam. V. Enkelmann and K. Müllen, Angew. Chem., Int. Ed Engl., 1992, 31, 878.
12. C. G. Screttas, G. A. Heropoulos, B. R. Steele and D. Bethell, Magn. Reson. Chem. 1998, 36, 656.
13. P. R. Markies, O. S. Akkerman, F. Bickelhaupt, W. J. J. Smeets and A. L. Spek, Adv. Organomet. Chem., 1991, 32, 147. We are indebted to Professor Bickelhaupt for also providing us with a preprint of a forthcoming up-dated review article.
14. Z. M. Hou, A. Fujita, Y. G. Zhang, T. Miyano, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1998, 120, 754; Z. Hou, T. Miyano, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1995, 117, 4421; Z. Hou, A. Fujita, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1996, 118, 7843: Z. Hou, X. Jia, M. Hoshino and Y. Wakatsuki, Angew. Chem., Int. Ed Engl., 1997, 36, 1292.
15. Z. M. Hou, A. Fujita, Y. G. Zhang, T. Miyano, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1998, 120, 754; Z. Hou, T. Miyano, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1995, 117, 4421; Z. Hou, A. Fujita, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1996, 118, 7843: Z. Hou, X. Jia, M. Hoshino and Y. Wakatsuki, Angew. Chem., Int. Ed Engl., 1997, 36, 1292.
16. Z. M. Hou, A. Fujita, Y. G. Zhang, T. Miyano, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1998, 120, 754; Z. Hou, T. Miyano, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1995, 117, 4421; Z. Hou, A. Fujita, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1996, 118, 7843: Z. Hou, X. Jia, M. Hoshino and Y. Wakatsuki, Angew. Chem., Int. Ed Engl., 1997, 36, 1292.
17. Z. M. Hou, A. Fujita, Y. G. Zhang, T. Miyano, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1998, 120, 754; Z. Hou, T. Miyano, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1995, 117, 4421; Z. Hou, A. Fujita, H. Yamazaki and Y. Wakatsuki, J. Am. Chem. Soc., 1996, 118, 7843: Z. Hou, X. Jia, M. Hoshino and Y. Wakatsuki, Angew. Chem., Int. Ed Engl., 1997, 36, 1292.
18. For recent work see: N. Doslik, T. Sixt and W. Kaim, Angew. Chem., Int. Ed., 1998, 37, 2403; A. Klein, S. Hasenzahl and W. Kaim, Organometallics, 1998, 17, 3532; A. Vlcek, Jr., F. Baumann, W. Kaim, F.-W. Grevels and F. Hartl, J. Chem. Soc., Dalton Trans., 1998, 215; A. Klein, S. Hasenzahl and W. Kaim, J. Chem. Soc., Perkin Trans. 2, 1997, 2573; S. Ernst, C. Vogler, A. Klein, W. Kaim and S. Zalis. Inorg. Chem., 1996, 35, 1295 and references therein.
19. For recent work see: N. Doslik, T. Sixt and W. Kaim, Angew. Chem., Int. Ed., 1998, 37, 2403; A. Klein, S. Hasenzahl and W. Kaim, Organometallics, 1998, 17, 3532; A. Vlcek, Jr., F. Baumann, W. Kaim, F.-W. Grevels and F. Hartl, J. Chem. Soc., Dalton Trans., 1998, 215; A. Klein, S. Hasenzahl and W. Kaim, J. Chem. Soc., Perkin Trans. 2, 1997, 2573; S. Ernst, C. Vogler, A. Klein, W. Kaim and S. Zalis. Inorg. Chem., 1996, 35, 1295 and references therein.
20. For recent work see: N. Doslik, T. Sixt and W. Kaim, Angew. Chem., Int. Ed., 1998, 37, 2403; A. Klein, S. Hasenzahl and W. Kaim, Organometallics, 1998, 17, 3532; A. Vlcek, Jr., F. Baumann, W. Kaim, F.-W. Grevels and F. Hartl, J. Chem. Soc., Dalton Trans., 1998, 215; A. Klein, S. Hasenzahl and W. Kaim, J. Chem. Soc., Perkin Trans. 2, 1997, 2573; S. Ernst, C. Vogler, A. Klein, W. Kaim and S. Zalis. Inorg. Chem., 1996, 35, 1295 and references therein.
21. For recent work see: N. Doslik, T. Sixt and W. Kaim, Angew. Chem., Int. Ed., 1998, 37, 2403; A. Klein, S. Hasenzahl and W. Kaim, Organometallics, 1998, 17, 3532; A. Vlcek, Jr., F. Baumann, W. Kaim, F.-W. Grevels and F. Hartl, J. Chem. Soc., Dalton Trans., 1998, 215; A. Klein, S. Hasenzahl and W. Kaim, J. Chem. Soc., Perkin Trans. 2, 1997, 2573; S. Ernst, C. Vogler, A. Klein, W. Kaim and S. Zalis. Inorg. Chem., 1996, 35, 1295 and references therein.
22. For recent work see: N. Doslik, T. Sixt and W. Kaim, Angew. Chem., Int. Ed., 1998, 37, 2403; A. Klein, S. Hasenzahl and W. Kaim, Organometallics, 1998, 17, 3532; A. Vlcek, Jr., F. Baumann, W. Kaim, F.-W. Grevels and F. Hartl, J. Chem. Soc., Dalton Trans., 1998, 215; A. Klein, S. Hasenzahl and W. Kaim, J. Chem. Soc., Perkin Trans. 2, 1997, 2573; S. Ernst, C. Vogler, A. Klein, W. Kaim and S. Zalis. Inorg. Chem., 1996, 35, 1295 and references therein.
23. N. C. Fletcher, T. C. Robinson, A. Behrendt, J. C. Jeffery, Z. R. Reeves and M. D. Ward, J. Chem. Soc., Dalton Trans., 1999, 2999; N. C. Harden, E. R. Humphrey, J. C. Jeffery, S.-M. Lee, M. Marcaccio, J. A. McCleverty, L. H. Rees and M. D. Ward, J. Chem. Soc., Dalton Trans., 1999, 2417.
24. N. C. Fletcher, T. C. Robinson, A. Behrendt, J. C. Jeffery, Z. R. Reeves and M. D. Ward, J. Chem. Soc., Dalton Trans., 1999, 2999; N. C. Harden, E. R. Humphrey, J. C. Jeffery, S.-M. Lee, M. Marcaccio, J. A. McCleverty, L. H. Rees and M. D. Ward, J. Chem. Soc., Dalton Trans., 1999, 2417.
25. C. G. Screttas, G. I. Ioannou and D. G. Georgiou, Russ. Chem. Bull., 1995, 44, 78.
26. S. Takeoka, K. Horiuchi and E. Tsushida, Solid State Ionics, 1992, 50, 175.
27. See for example, S. R. Zhu and T. Cohen, Tetrahedron, 1997, 53, 17607; G. H. Lee, S. J. Ha, I. K. Yoon and C. S. Pak, Tetrahedron Lett., 1999, 40, 2581; C. S. Salteris, I. D. Kostas, M. Micha-Screttas, B. R. Steele, G. A. Heropoulos, C. G. Screttas and A. Terzis, J. Organomet. Chem., 1999, 590, 63.
28. See for example, S. R. Zhu and T. Cohen, Tetrahedron, 1997, 53, 17607; G. H. Lee, S. J. Ha, I. K. Yoon and C. S. Pak, Tetrahedron Lett., 1999, 40, 2581; C. S. Salteris, I. D. Kostas, M. Micha-Screttas, B. R. Steele, G. A. Heropoulos, C. G. Screttas and A. Terzis, J. Organomet. Chem., 1999, 590, 63.
29. See for example, S. R. Zhu and T. Cohen, Tetrahedron, 1997, 53, 17607; G. H. Lee, S. J. Ha, I. K. Yoon and C. S. Pak, Tetrahedron Lett., 1999, 40, 2581; C. S. Salteris, I. D. Kostas, M. Micha-Screttas, B. R. Steele, G. A. Heropoulos, C. G. Screttas and A. Terzis, J. Organomet. Chem., 1999, 590, 63.
30. H. S. Sorensen and K. Daasbjerg, Acta Chem. Scand., Sci: A, 52, 51; C. Galli and P. Gentili, Acta Chem. Scand., Ser. A, 1998, 52, 67 ; T. Holm, J. Am. Chem. Soc., 1999, 121, 515; S. Shaik, D. Danovich, G. N. Sastry, P. Y. Ayala and H. B. Schlegel, J. Am. Chem. Soc., 1997, 119, 9237.
31. H. S. Sorensen and K. Daasbjerg, Acta Chem. Scand., Sci: A, 52, 51; C. Galli and P. Gentili, Acta Chem. Scand., Ser. A, 1998, 52, 67 ; T. Holm, J. Am. Chem. Soc., 1999, 121, 515; S. Shaik, D. Danovich, G. N. Sastry, P. Y. Ayala and H. B. Schlegel, J. Am. Chem. Soc., 1997, 119, 9237.
32. H. S. Sorensen and K. Daasbjerg, Acta Chem. Scand., Sci: A, 52, 51; C. Galli and P. Gentili, Acta Chem. Scand., Ser. A, 1998, 52, 67 ; T. Holm, J. Am. Chem. Soc., 1999, 121, 515; S. Shaik, D. Danovich, G. N. Sastry, P. Y. Ayala and H. B. Schlegel, J. Am. Chem. Soc., 1997, 119, 9237.
33. H. S. Sorensen and K. Daasbjerg, Acta Chem. Scand., Sci: A, 52, 51; C. Galli and P. Gentili, Acta Chem. Scand., Ser. A, 1998, 52, 67 ; T. Holm, J. Am. Chem. Soc., 1999, 121, 515; S. Shaik, D. Danovich, G. N. Sastry, P. Y. Ayala and H. B. Schlegel, J. Am. Chem. Soc., 1997, 119, 9237.
34. M. Micha-Screttas, G. A. Heropoulos and B. R. Steele, J. Chem. Soc., Perkin Trans. 2, 1999, 1443.
35. C. G. Screttas and M. Micha-Screttas, J. Am. Chem. Soc., 1987, 109, 7573.
36. C. G. Screttas and M. Micha-Screttas, J. Org. Chem., 1981, 46, 993; J. Org. Chem., 1983, 48, 153.
37. C. G. Screttas and M. Micha-Screttas, J. Org. Chem., 1981, 46, 993; J. Org. Chem., 1983, 48, 153.
38. The observation that reaction between the diamagnetic complex with methyl iodide led to formation of benzophenone is consistent with this interpretation. Indeed, electron transfer from the pinacolate dianion causes fragmentation via the formation of an oxygen-centred radical and a β-scission process, see ref. 8.
39. J. March, Advanced Organic Chemistry, Reactions, Mechanisms and Structures, Fourth Edition, John Wiley and Sons, Inc., New York, 1992, p. 1225.
40. C. G. Screttas and M. Micha-Screttas, J. Organomet. Chem., 1985, 292, 325.
41. th Edn., CRC Press, Cleveland, Ohio, 1973-1974, Sect. C-2.