C8 and C12 sp Carbon Chains That Span Two Platinum Atoms: The First Structurally Characterized 1,3,5,7,9,11-Hexayne

Organometallics

Volumn 18, Issue 17, 1999, Pages 3261-3263

  Peters, Thomas B ^a   Bohling, James C ^a   Arif, Atta M ^a   Gladysz, J A ^a,b  

^a UNIVERSITY OF UTAH   (United States)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001698461     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990448c     Document Type: Article

References (41)

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6. Full papers from our laboratory: (a) Weng, W.; Bartik, T.; Brady, M.; Bartik, B.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1995, 117, 11922. (b) Brady, M.; Weng, W.; Zhou, Y.; Seyler, J. W.; Amoroso, A. J.; Arif, A. M.; Böhme, M.; Frenking, G.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 119, 775. (c) Falloon, S. B.; Szafert, S.; Arif, A. M.; Gladysz, J. A. Chem. Eur. J. 1998, 4, 1033. (d) Bartik, T.; Weng, W.; Ramsden, J. A.; Szafert, S.; Falloon, S. B.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1998, 120, 11071. (e) Dembinski, R.; Bartik, T.; Bartik, B.; Jaeger, M.; Gladysz, J. A. Submitted for publication (communication: Bartik, T.; Bartik, B.; Brady, M.; Dembinski, R.; Gladysz, J. A. Angew. Chem. 1996, 108, 467; Angew. Chem., Int. Ed. 1996, 35, 414).
7. Full papers from our laboratory: (a) Weng, W.; Bartik, T.; Brady, M.; Bartik, B.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1995, 117, 11922. (b) Brady, M.; Weng, W.; Zhou, Y.; Seyler, J. W.; Amoroso, A. J.; Arif, A. M.; Böhme, M.; Frenking, G.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 119, 775. (c) Falloon, S. B.; Szafert, S.; Arif, A. M.; Gladysz, J. A. Chem. Eur. J. 1998, 4, 1033. (d) Bartik, T.; Weng, W.; Ramsden, J. A.; Szafert, S.; Falloon, S. B.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1998, 120, 11071. (e) Dembinski, R.; Bartik, T.; Bartik, B.; Jaeger, M.; Gladysz, J. A. Submitted for publication (communication: Bartik, T.; Bartik, B.; Brady, M.; Dembinski, R.; Gladysz, J. A. Angew. Chem. 1996, 108, 467; Angew. Chem., Int. Ed. 1996, 35, 414).
8. Full papers from our laboratory: (a) Weng, W.; Bartik, T.; Brady, M.; Bartik, B.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1995, 117, 11922. (b) Brady, M.; Weng, W.; Zhou, Y.; Seyler, J. W.; Amoroso, A. J.; Arif, A. M.; Böhme, M.; Frenking, G.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 119, 775. (c) Falloon, S. B.; Szafert, S.; Arif, A. M.; Gladysz, J. A. Chem. Eur. J. 1998, 4, 1033. (d) Bartik, T.; Weng, W.; Ramsden, J. A.; Szafert, S.; Falloon, S. B.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1998, 120, 11071. (e) Dembinski, R.; Bartik, T.; Bartik, B.; Jaeger, M.; Gladysz, J. A. Submitted for publication (communication: Bartik, T.; Bartik, B.; Brady, M.; Dembinski, R.; Gladysz, J. A. Angew. Chem. 1996, 108, 467; Angew. Chem., Int. Ed. 1996, 35, 414).
9. Full papers from our laboratory: (a) Weng, W.; Bartik, T.; Brady, M.; Bartik, B.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1995, 117, 11922. (b) Brady, M.; Weng, W.; Zhou, Y.; Seyler, J. W.; Amoroso, A. J.; Arif, A. M.; Böhme, M.; Frenking, G.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 119, 775. (c) Falloon, S. B.; Szafert, S.; Arif, A. M.; Gladysz, J. A. Chem. Eur. J. 1998, 4, 1033. (d) Bartik, T.; Weng, W.; Ramsden, J. A.; Szafert, S.; Falloon, S. B.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1998, 120, 11071. (e) Dembinski, R.; Bartik, T.; Bartik, B.; Jaeger, M.; Gladysz, J. A. Submitted for publication (communication: Bartik, T.; Bartik, B.; Brady, M.; Dembinski, R.; Gladysz, J. A. Angew. Chem. 1996, 108, 467; Angew. Chem., Int. Ed. 1996, 35, 414).
10. Full papers from our laboratory: (a) Weng, W.; Bartik, T.; Brady, M.; Bartik, B.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1995, 117, 11922. (b) Brady, M.; Weng, W.; Zhou, Y.; Seyler, J. W.; Amoroso, A. J.; Arif, A. M.; Böhme, M.; Frenking, G.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 119, 775. (c) Falloon, S. B.; Szafert, S.; Arif, A. M.; Gladysz, J. A. Chem. Eur. J. 1998, 4, 1033. (d) Bartik, T.; Weng, W.; Ramsden, J. A.; Szafert, S.; Falloon, S. B.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1998, 120, 11071. (e) Dembinski, R.; Bartik, T.; Bartik, B.; Jaeger, M.; Gladysz, J. A. Submitted for publication (communication: Bartik, T.; Bartik, B.; Brady, M.; Dembinski, R.; Gladysz, J. A. Angew. Chem. 1996, 108, 467; Angew. Chem., Int. Ed. 1996, 35, 414).
11. Full papers from our laboratory: (a) Weng, W.; Bartik, T.; Brady, M.; Bartik, B.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1995, 117, 11922. (b) Brady, M.; Weng, W.; Zhou, Y.; Seyler, J. W.; Amoroso, A. J.; Arif, A. M.; Böhme, M.; Frenking, G.; Gladysz, J. A. J. Am. Chem. Soc. 1987, 119, 775. (c) Falloon, S. B.; Szafert, S.; Arif, A. M.; Gladysz, J. A. Chem. Eur. J. 1998, 4, 1033. (d) Bartik, T.; Weng, W.; Ramsden, J. A.; Szafert, S.; Falloon, S. B.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1998, 120, 11071. (e) Dembinski, R.; Bartik, T.; Bartik, B.; Jaeger, M.; Gladysz, J. A. Submitted for publication (communication: Bartik, T.; Bartik, B.; Brady, M.; Dembinski, R.; Gladysz, J. A. Angew. Chem. 1996, 108, 467; Angew. Chem., Int. Ed. 1996, 35, 414).
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18. (c) Carbon Rich Compounds II: Macrocyclic Oligoacetylenes and Other Linearly Conjugated Systems; de Meijre, A., Ed.; Topics in Current Chemistry 201; Springer-Verlag: Berlin, 1999.
19. 32 polyalkynediyl systems with tert-butyl, silyl, or cyano end groups, see the following lead papers and references therein: (a) Eastmond, R.; Johnson, T. R.; Walton, D. R. M. Tetrahedron 1972, 28, 4601. (b) Johnson, T. R.; Walton, D. R. M. Tetrahedron 1972, 28, 6221. (c) Schermann, G.; Grösser, T.; Hampel, F.; Hirsch, A. Chem. Eur. J. 1997, 3, 1105.
20. 32 polyalkynediyl systems with tert-butyl, silyl, or cyano end groups, see the following lead papers and references therein: (a) Eastmond, R.; Johnson, T. R.; Walton, D. R. M. Tetrahedron 1972, 28, 4601. (b) Johnson, T. R.; Walton, D. R. M. Tetrahedron 1972, 28, 6221. (c) Schermann, G.; Grösser, T.; Hampel, F.; Hirsch, A. Chem. Eur. J. 1997, 3, 1105.
21. 32 polyalkynediyl systems with tert-butyl, silyl, or cyano end groups, see the following lead papers and references therein: (a) Eastmond, R.; Johnson, T. R.; Walton, D. R. M. Tetrahedron 1972, 28, 4601. (b) Johnson, T. R.; Walton, D. R. M. Tetrahedron 1972, 28, 6221. (c) Schermann, G.; Grösser, T.; Hampel, F.; Hirsch, A. Chem. Eur. J. 1997, 3, 1105.
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25. (c) Homman, K.-H. Angew. Chem. 1998,110, 2572; Angew. Chem., Int. Ed. 1998, 37, 2435.
26. All crystallographically characterized 1,3,5,7-tetraynes (seven) and 1,3,5,7,9-pentaynes (one) are tabulated in the following papers: (a) Bartik, B.; Dembinski, R.; Bartik, T.; Arif, A. M.; Gladysz, J. A. New J. Chem. 1997, 21, 739. (b) Dembinski, R.; Lis, T.; Szafert, S.; Mayne, C. L.; Bartik, T.; Gladysz, J. A. J. Organomet. Chem. 1999, 578, 229.
27. All crystallographically characterized 1,3,5,7-tetraynes (seven) and 1,3,5,7,9-pentaynes (one) are tabulated in the following papers: (a) Bartik, B.; Dembinski, R.; Bartik, T.; Arif, A. M.; Gladysz, J. A. New J. Chem. 1997, 21, 739. (b) Dembinski, R.; Lis, T.; Szafert, S.; Mayne, C. L.; Bartik, T.; Gladysz, J. A. J. Organomet. Chem. 1999, 578, 229.
28. 8d
29. (b) Clark, H. C.; Manzer, L. E. J. Organomet. Chem. 1973, 59, 411.
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31. (d) Alternative synthesis: Ertl, J.; Grafl, D.; Brune. H. A. Z. Naturforsch. 1982, 37B, 1082.
32. All new complexes were characterized by IR and NMR spectroscopy (and many by additional means), as detailed in the Supporting Information. Most gave correct microanalyses.
33. Pregosin, P. S.; Venanzi, L. M. Chem. Br. 1978, 276.
34. (a) Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: New York, 1981; p 146.
35. (b) Ibid., p 136.
36. Related platinum butadiynyl complexes have been similarly prepared: (a) Fiyikura, Y.; Hagihara, N.; Sonogashira, K.; Takahashi, S.; Toyoshima, N. J. Organomet. Chem. 1978, 145, 101. (b) Bruce, M. I.; Ke, M.; Low, P. J. J. Chem. Soc., Chem. Commun. 1996, 2405. (c) AlQaisi, S. M.; Galat, K. J.; Chai, M.; Ray, D. G., III; Rinaldi, P. L.; Tessier, C. A.; Youngs, W. J. J. Am. Chem. Soc. 1998, 120, 12149.
37. Related platinum butadiynyl complexes have been similarly prepared: (a) Fiyikura, Y.; Hagihara, N.; Sonogashira, K.; Takahashi, S.; Toyoshima, N. J. Organomet. Chem. 1978, 145, 101. (b) Bruce, M. I.; Ke, M.; Low, P. J. J. Chem. Soc., Chem. Commun. 1996, 2405. (c) AlQaisi, S. M.; Galat, K. J.; Chai, M.; Ray, D. G., III; Rinaldi, P. L.; Tessier, C. A.; Youngs, W. J. J. Am. Chem. Soc. 1998, 120, 12149.
38. Related platinum butadiynyl complexes have been similarly prepared: (a) Fiyikura, Y.; Hagihara, N.; Sonogashira, K.; Takahashi, S.; Toyoshima, N. J. Organomet. Chem. 1978, 145, 101. (b) Bruce, M. I.; Ke, M.; Low, P. J. J. Chem. Soc., Chem. Commun. 1996, 2405. (c) AlQaisi, S. M.; Galat, K. J.; Chai, M.; Ray, D. G., III; Rinaldi, P. L.; Tessier, C. A.; Youngs, W. J. J. Am. Chem. Soc. 1998, 120, 12149.
39. 2PtC≡CR complexes: (a) Furlani, A.; Licoccia, S.; Russo, M. V.; Villa, A. C.; Guastini, C. J. Chem. Soc., Dalton Trans. 1984, 2197. (b) Lewis, J.; Long, N. J.; Raithby, P. R.; Sheilds, G. P.; Wong, W.-Y.; Younus, M. J. Chem. Soc., Dalton Trans. 1997, 4283. (c) Bohling, J. C.; Peters, T. B.; Arif, A. M.; Hampel, F.; Gladysz, J. A. In Coordination Chemistry at the Turn of the Century; Ondrejoviç, G., Sirota, A., Eds.; Slovak Technical University Press: Bratislava, Slovakia, 1999; p 47.
40. 2PtC≡CR complexes: (a) Furlani, A.; Licoccia, S.; Russo, M. V.; Villa, A. C.; Guastini, C. J. Chem. Soc., Dalton Trans. 1984, 2197. (b) Lewis, J.; Long, N. J.; Raithby, P. R.; Sheilds, G. P.; Wong, W.-Y.; Younus, M. J. Chem. Soc., Dalton Trans. 1997, 4283. (c) Bohling, J. C.; Peters, T. B.; Arif, A. M.; Hampel, F.; Gladysz, J. A. In Coordination Chemistry at the Turn of the Century; Ondrejoviç, G., Sirota, A., Eds.; Slovak Technical University Press: Bratislava, Slovakia, 1999; p 47.
41. 2PtC≡CR complexes: (a) Furlani, A.; Licoccia, S.; Russo, M. V.; Villa, A. C.; Guastini, C. J. Chem. Soc., Dalton Trans. 1984, 2197. (b) Lewis, J.; Long, N. J.; Raithby, P. R.; Sheilds, G. P.; Wong, W.-Y.; Younus, M. J. Chem. Soc., Dalton Trans. 1997, 4283. (c) Bohling, J. C.; Peters, T. B.; Arif, A. M.; Hampel, F.; Gladysz, J. A. In Coordination Chemistry at the Turn of the Century; Ondrejoviç, G., Sirota, A., Eds.; Slovak Technical University Press: Bratislava, Slovakia, 1999; p 47.