Mechanism of formation of threaded Ar2Zn(18-crown-6) species

Organometallics

Volumn 17, Issue 15, 1998, Pages 3204-3209

  Chubb, John E ^a   Richey Jr , Herman G ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011529921     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9801960     Document Type: Article

References (24)

1. Markies, P. R.; Nomoto, T.; Akkerman, O. S.; Bickelhaupt, F. J. Am. Chem. Soc. 1988, 110, 4845.
2. Pajerski, A. D.; BergStresser, G. L.; Parvez, M.; Richey, H. G., Jr. J. Am. Chem. Soc. 1988, 110, 4844.
3. For a review of interactions of organomagnesium and organozinc compounds with macrocyclic compounds, see: Richey, H. G., Jr. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 1 (G. W. Gokel, Ed.), Chapter 21.
4. Gruter, G.-J. M.; de Kanter, F. J. J.; Markies, P. R.; Nomoto, T.; Akkerman, O. S.; Bickelhaupt, F. J. Am. Chem. Soc. 1993, 115, 12179.
5. 2Hg and crown ethers; the crown ethers were much larger, however, and the pattern of results suggested that formation was by direct passage of intact organomercury compound into a crown ether cavity. Rebek, J., Jr.; Marshall, L. J. Am. Chem. Soc. 1983, 105, 6668. Onan, K.; Rebek, J., Jr.; Costello, T.; Marshall, L. J. Am. Chem. Soc. 1983, 105, 6759. Rebek, J., Jr.; Costello, T.; Marshall, L.; Wattley, R.; Gadwood, R. C.; Onan, K. J. Am. Chem. Soc. 1985, 107, 7481. Rebek, J., Jr.; Luis, S. V.; Marshall, L. R. J. Am. Chem. Soc. 1986, 108, 5011. Luis, S. V.; Burguete, M. I.; Salvador, R. V. J. Inclusion Phenom. Mol. Recognit. Chem. 1991, 10, 341.
6. 2Hg and crown ethers; the crown ethers were much larger, however, and the pattern of results suggested that formation was by direct passage of intact organomercury compound into a crown ether cavity. Rebek, J., Jr.; Marshall, L. J. Am. Chem. Soc. 1983, 105, 6668. Onan, K.; Rebek, J., Jr.; Costello, T.; Marshall, L. J. Am. Chem. Soc. 1983, 105, 6759. Rebek, J., Jr.; Costello, T.; Marshall, L.; Wattley, R.; Gadwood, R. C.; Onan, K. J. Am. Chem. Soc. 1985, 107, 7481. Rebek, J., Jr.; Luis, S. V.; Marshall, L. R. J. Am. Chem. Soc. 1986, 108, 5011. Luis, S. V.; Burguete, M. I.; Salvador, R. V. J. Inclusion Phenom. Mol. Recognit. Chem. 1991, 10, 341.
7. 2Hg and crown ethers; the crown ethers were much larger, however, and the pattern of results suggested that formation was by direct passage of intact organomercury compound into a crown ether cavity. Rebek, J., Jr.; Marshall, L. J. Am. Chem. Soc. 1983, 105, 6668. Onan, K.; Rebek, J., Jr.; Costello, T.; Marshall, L. J. Am. Chem. Soc. 1983, 105, 6759. Rebek, J., Jr.; Costello, T.; Marshall, L.; Wattley, R.; Gadwood, R. C.; Onan, K. J. Am. Chem. Soc. 1985, 107, 7481. Rebek, J., Jr.; Luis, S. V.; Marshall, L. R. J. Am. Chem. Soc. 1986, 108, 5011. Luis, S. V.; Burguete, M. I.; Salvador, R. V. J. Inclusion Phenom. Mol. Recognit. Chem. 1991, 10, 341.
8. 2Hg and crown ethers; the crown ethers were much larger, however, and the pattern of results suggested that formation was by direct passage of intact organomercury compound into a crown ether cavity. Rebek, J., Jr.; Marshall, L. J. Am. Chem. Soc. 1983, 105, 6668. Onan, K.; Rebek, J., Jr.; Costello, T.; Marshall, L. J. Am. Chem. Soc. 1983, 105, 6759. Rebek, J., Jr.; Costello, T.; Marshall, L.; Wattley, R.; Gadwood, R. C.; Onan, K. J. Am. Chem. Soc. 1985, 107, 7481. Rebek, J., Jr.; Luis, S. V.; Marshall, L. R. J. Am. Chem. Soc. 1986, 108, 5011. Luis, S. V.; Burguete, M. I.; Salvador, R. V. J. Inclusion Phenom. Mol. Recognit. Chem. 1991, 10, 341.
9. 2Hg and crown ethers; the crown ethers were much larger, however, and the pattern of results suggested that formation was by direct passage of intact organomercury compound into a crown ether cavity. Rebek, J., Jr.; Marshall, L. J. Am. Chem. Soc. 1983, 105, 6668. Onan, K.; Rebek, J., Jr.; Costello, T.; Marshall, L. J. Am. Chem. Soc. 1983, 105, 6759. Rebek, J., Jr.; Costello, T.; Marshall, L.; Wattley, R.; Gadwood, R. C.; Onan, K. J. Am. Chem. Soc. 1985, 107, 7481. Rebek, J., Jr.; Luis, S. V.; Marshall, L. R. J. Am. Chem. Soc. 1986, 108, 5011. Luis, S. V.; Burguete, M. I.; Salvador, R. V. J. Inclusion Phenom. Mol. Recognit. Chem. 1991, 10, 341.
10. Squiller, E. P.; Whittle, R. R.; Richey, H. G., Jr. J. Am. Chem. Soc. 1985, 107, 432. Richey, H. G., Jr.; Kushlan, D. M. J. Am. Chem Soc. 1987, 109, 2510.
11. Squiller, E. P.; Whittle, R. R.; Richey, H. G., Jr. J. Am. Chem. Soc. 1985, 107, 432. Richey, H. G., Jr.; Kushlan, D. M. J. Am. Chem Soc. 1987, 109, 2510.
12. Pajerski, A. D.; Parvez, M.; Richey, H. G., Jr. J. Am. Chem. Soc. 1988, 110, 2660.
13. Fabicon, R. M.; Pajerski, A. D.; Richey, H. G., Jr. J. Am. Chem. Soc. 1991, 113, 6680. Also see: Tang, H.; Richey, H. G., Jr. Organometallics 1996, 15, 4891.
14. Fabicon, R. M.; Pajerski, A. D.; Richey, H. G., Jr. J. Am. Chem. Soc. 1991, 113, 6680. Also see: Tang, H.; Richey, H. G., Jr. Organometallics 1996, 15, 4891.
15. Fabicon, R. M. Ph.D. Dissertation, The Pennsylvania State University, 1991.
16. 2Zn concentrations of 0.02-0.06 M and 18-crown-6 concentrations of 0.01-0.15 M.
17. For information on coordination of organozinc compounds to ether oxygens, see: Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Chapter 16. O'Brien, P. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 3, Chapter 4.
18. For information on coordination of organozinc compounds to ether oxygens, see: Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Chapter 16. O'Brien, P. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 3, Chapter 4.
19. 1H NMR spectra.
20. Erratic results in earlier efforts [ref 9 and BergStresser, G. L. M.S. Dissertation, The Pennsylvania State University, 1986] to study equilibria of diorganozinc compounds and 18-crown-6 with rotaxanes may be the consequence of not being aware of the large effect of the reactant ratio on the rate of approach to equilibrium.
21. 0).
22. For example: de Graaf, P. W. J.; Boersma, J.; van der Kerk, G. J. M. J. Organomet. Chem. 1977, 127, 391.
23. Sheverdina, N. I.; Paleeva, I. E.; Zaitseva, N. A.; Kocheskov, K. A. Dokl. Akad. Nauk SSSR 1964, 155, 623; Chem. Abstr. 1964, 60, 14531.
24. Sheverdina, N. I.; Paleeva, I. E.; Zaitseva, N. A.; Kocheskov, K. A. Dokl. Akad. Nauk SSSR 1964, 155, 623; Chem. Abstr. 1964, 60, 14531.