A novel 1,2-aryl migration in metallanethione: Unusual formation of an aryl(arylthio)plumbylene from a plumbanethione

Organometallics

Volumn 16, Issue 20, 1997, Pages 4237-4239

  Kano, Naokazu ^a   Tokitoh, Norihiro ^a   Okazaki, Renji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000622847     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9705564     Document Type: Article

References (31)

1. (a) Raabe, G.; Michl, J. Chem. Rev. 1985, 85, 419.
2. (b) Petz, W. Chem. Rev. 1986, 86, 1019.
3. (c) Lappert, M. F.; Rowe, R. S. Coord. Chem. Rev. 1990, 100, 267.
4. (d) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283.
5. (e) Neumann, W. P. Chem. Rev. 1991, 91, 311.
6. (f) Tsumuraya, T.; Batcheller, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 902.
7. For stable plumbylenes, see: (a) Davidson, P. J.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1973, 317. (b) Harris, D. H.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1974, 895. (c) Brooker, S.; Buijink, J.-K.; Edelmann, F. T. Organometallics 1991, 10, 25. (d) Klinkhammer, K. W.; Schwartz, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 1334. (e) Driess, M.; Janoschek, R.; Pritzkow, H.; Rell, S.; Winkler, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1614. (f) Simons, R. S.; Pu, L.; Olmstead, M. M.; Power, P. P. Organometallics 1997, 9, 1920.
8. For stable plumbylenes, see: (a) Davidson, P. J.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1973, 317. (b) Harris, D. H.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1974, 895. (c) Brooker, S.; Buijink, J.-K.; Edelmann, F. T. Organometallics 1991, 10, 25. (d) Klinkhammer, K. W.; Schwartz, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 1334. (e) Driess, M.; Janoschek, R.; Pritzkow, H.; Rell, S.; Winkler, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1614. (f) Simons, R. S.; Pu, L.; Olmstead, M. M.; Power, P. P. Organometallics 1997, 9, 1920.
9. For stable plumbylenes, see: (a) Davidson, P. J.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1973, 317. (b) Harris, D. H.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1974, 895. (c) Brooker, S.; Buijink, J.-K.; Edelmann, F. T. Organometallics 1991, 10, 25. (d) Klinkhammer, K. W.; Schwartz, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 1334. (e) Driess, M.; Janoschek, R.; Pritzkow, H.; Rell, S.; Winkler, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1614. (f) Simons, R. S.; Pu, L.; Olmstead, M. M.; Power, P. P. Organometallics 1997, 9, 1920.
10. For stable plumbylenes, see: (a) Davidson, P. J.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1973, 317. (b) Harris, D. H.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1974, 895. (c) Brooker, S.; Buijink, J.-K.; Edelmann, F. T. Organometallics 1991, 10, 25. (d) Klinkhammer, K. W.; Schwartz, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 1334. (e) Driess, M.; Janoschek, R.; Pritzkow, H.; Rell, S.; Winkler, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1614. (f) Simons, R. S.; Pu, L.; Olmstead, M. M.; Power, P. P. Organometallics 1997, 9, 1920.
11. For stable plumbylenes, see: (a) Davidson, P. J.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1973, 317. (b) Harris, D. H.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1974, 895. (c) Brooker, S.; Buijink, J.-K.; Edelmann, F. T. Organometallics 1991, 10, 25. (d) Klinkhammer, K. W.; Schwartz, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 1334. (e) Driess, M.; Janoschek, R.; Pritzkow, H.; Rell, S.; Winkler, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1614. (f) Simons, R. S.; Pu, L.; Olmstead, M. M.; Power, P. P. Organometallics 1997, 9, 1920.
12. For stable plumbylenes, see: (a) Davidson, P. J.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1973, 317. (b) Harris, D. H.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1974, 895. (c) Brooker, S.; Buijink, J.-K.; Edelmann, F. T. Organometallics 1991, 10, 25. (d) Klinkhammer, K. W.; Schwartz, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 1334. (e) Driess, M.; Janoschek, R.; Pritzkow, H.; Rell, S.; Winkler, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1614. (f) Simons, R. S.; Pu, L.; Olmstead, M. M.; Power, P. P. Organometallics 1997, 9, 1920.
13. For three- or four-coordinate heteroleptic plumbylenes, see: (a) Eaborn, C.; Izod, K.; Hitchcock, P. B.; Sözerli, S. E.; Smith, J. D. J. Chem. Soc., Chem. Commun. 1995, 1829. (b) Balch, A.; Oram, D. E. Inorg. Chem. 1987, 26, 1906.
14. For three- or four-coordinate heteroleptic plumbylenes, see: (a) Eaborn, C.; Izod, K.; Hitchcock, P. B.; Sözerli, S. E.; Smith, J. D. J. Chem. Soc., Chem. Commun. 1995, 1829. (b) Balch, A.; Oram, D. E. Inorg. Chem. 1987, 26, 1906.
15. (a) Tokitoh, N.; Matsumoto, T.; Manmaru, K.; Okazaki, R. J. Am. Chem. Soc. 1993, 115, 8855.
16. (b) Matsumoto, T.; Tokitoh, N.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2316.
17. (c) Suzuki, H.; Tokitoh, N.; Nagase, S.; Okazaki, R. J. Am. Chem. Soc. 1994, 116, 11578.
18. (d) Tokitoh, N.; Matsumoto, T.; Okazaki, R. J. Am. Chem. Soc. 1997, 119, 2337.
19. Kano, N.; Tokitoh, N.; Okazaki, R. Chem. Lett. 1997, 277.
20. (a) Tokitoh, N.; Kano, N.; Shibata, K.; Okazaki, R. Phosphorous, Sulfur Silicon Relat. Elem. 1994, 93-94, 189.
21. (b) Tokitoh, N.; Kano, N.; Shibata, K.; Okazaki, R. Organometallics 1995, 14, 3121.
22. 12: C, 55.50; H, 10.18; S, 5.49. Found: C, 55.20; H, 9.95; S, 5.80.
23. 2O, was 74%. The authors thank the editor for suggesting this experiment.
24. w) = 0.047 (0.053) with GOF = 1.23. The lead and sulfur atoms were located at disordered positions in two sites with 1:1 occupancy factors. Although the molecule of compound 2 has no center of symmetry, the crystal structure of 2 showed the appearance of an inversion center due to the disordered structure. The structural refinement with a space group of P1 (Z=1) failed and diverged. All calculations were performed using the TEXSAN crystallographic software package of Molecular Structure Corp. Atomic coodinates, bond lengths and angles, and thermal parameters have been deposited at Cambridge Crystallographic Data Centre.
25. Sheldrick, G. M. SHELXS-86, Program for Crystal Structure Determination; University of Göttingen: Göttingen, Germany, 1986.
26. An arylthioplumbylene tends to oligomerize. See, for example: Hitchcock, P. B.; Lappert, M. F.; Samways, B. J.; Weinburg, E. L. J. Chem. Soc., Chem. Commun. 1983, 1492.
27. Greenwood, N. N.; Earnshaw, A. Chemistry of the Elements; Pergamon: Oxford, England, 1984; p 431.
28. We have previously reported that diarylplumbylene could be trapped by methyl iodide to give the corresponding iodomethylplumbane. See ref 6.
29. (a) Tokitoh, N.; Matsuhashi, Y.; Goto, M.; Okazaki, R. Chem. Lett. 1992, 1595.
30. (b) Matsuhashi, Y.; Tokitoh, N.; Okazaki, R. Organometallics 1993, 12, 2573.
31. Kapp, J.; Remko, M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1996, 118, 5745.