Synthesis and crystallographic characterization of a platinadehydrobenzo[19]annulene

Organometallics

Volumn 16, Issue 21, 1997, Pages 4505-4507

  Pak, Joshua J ^a   Weakley, Timothy J R ^a   Haley, Michael M ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000664979     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970661d     Document Type: Article

References (35)

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23. For some recent examples, see: (a) Tykwinski, R. R.; Stang, P. J. Organometallics 1994, 13, 3203. (b) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923. (c) Lichtenberger, D. L.; Renshaw, S. K.; Bullock, R. M. J. Am. Chem. Soc. 1993, 115, 3276. (d) Lichtenberger, D. L.; Renshaw, S. K.; Wong, A.; Tagge, C. D. Organometallics 1993, 12, 3522. (e) Khan, M. S.; Davies, S. J.; Kakkar, A. K.; Schwartz, D.; Lin, B.; Johnson, B. F. G.; Lewis, J. J. Organomet. Chem. 1992, 424, 87. (f) Lewis, J.; Khan, M. S.; Kakkar, A. K.; Johnson, B. F. G.; Marder, T. B.; Fyfe, H. B.; Wittmann, F.; Friend, R. H.; Dray, A. E. J. Organomet. Chem. 1992, 425, 165.
24. For some recent examples, see: (a) Tykwinski, R. R.; Stang, P. J. Organometallics 1994, 13, 3203. (b) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923. (c) Lichtenberger, D. L.; Renshaw, S. K.; Bullock, R. M. J. Am. Chem. Soc. 1993, 115, 3276. (d) Lichtenberger, D. L.; Renshaw, S. K.; Wong, A.; Tagge, C. D. Organometallics 1993, 12, 3522. (e) Khan, M. S.; Davies, S. J.; Kakkar, A. K.; Schwartz, D.; Lin, B.; Johnson, B. F. G.; Lewis, J. J. Organomet. Chem. 1992, 424, 87. (f) Lewis, J.; Khan, M. S.; Kakkar, A. K.; Johnson, B. F. G.; Marder, T. B.; Fyfe, H. B.; Wittmann, F.; Friend, R. H.; Dray, A. E. J. Organomet. Chem. 1992, 425, 165.
25. For some recent examples, see: (a) Tykwinski, R. R.; Stang, P. J. Organometallics 1994, 13, 3203. (b) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923. (c) Lichtenberger, D. L.; Renshaw, S. K.; Bullock, R. M. J. Am. Chem. Soc. 1993, 115, 3276. (d) Lichtenberger, D. L.; Renshaw, S. K.; Wong, A.; Tagge, C. D. Organometallics 1993, 12, 3522. (e) Khan, M. S.; Davies, S. J.; Kakkar, A. K.; Schwartz, D.; Lin, B.; Johnson, B. F. G.; Lewis, J. J. Organomet. Chem. 1992, 424, 87. (f) Lewis, J.; Khan, M. S.; Kakkar, A. K.; Johnson, B. F. G.; Marder, T. B.; Fyfe, H. B.; Wittmann, F.; Friend, R. H.; Dray, A. E. J. Organomet. Chem. 1992, 425, 165.
26. For some recent examples, see: (a) Tykwinski, R. R.; Stang, P. J. Organometallics 1994, 13, 3203. (b) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923. (c) Lichtenberger, D. L.; Renshaw, S. K.; Bullock, R. M. J. Am. Chem. Soc. 1993, 115, 3276. (d) Lichtenberger, D. L.; Renshaw, S. K.; Wong, A.; Tagge, C. D. Organometallics 1993, 12, 3522. (e) Khan, M. S.; Davies, S. J.; Kakkar, A. K.; Schwartz, D.; Lin, B.; Johnson, B. F. G.; Lewis, J. J. Organomet. Chem. 1992, 424, 87. (f) Lewis, J.; Khan, M. S.; Kakkar, A. K.; Johnson, B. F. G.; Marder, T. B.; Fyfe, H. B.; Wittmann, F.; Friend, R. H.; Dray, A. E. J. Organomet. Chem. 1992, 425, 165.
27. For some recent examples, see: (a) Tykwinski, R. R.; Stang, P. J. Organometallics 1994, 13, 3203. (b) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923. (c) Lichtenberger, D. L.; Renshaw, S. K.; Bullock, R. M. J. Am. Chem. Soc. 1993, 115, 3276. (d) Lichtenberger, D. L.; Renshaw, S. K.; Wong, A.; Tagge, C. D. Organometallics 1993, 12, 3522. (e) Khan, M. S.; Davies, S. J.; Kakkar, A. K.; Schwartz, D.; Lin, B.; Johnson, B. F. G.; Lewis, J. J. Organomet. Chem. 1992, 424, 87. (f) Lewis, J.; Khan, M. S.; Kakkar, A. K.; Johnson, B. F. G.; Marder, T. B.; Fyfe, H. B.; Wittmann, F.; Friend, R. H.; Dray, A. E. J. Organomet. Chem. 1992, 425, 165.
28. For some recent examples, see: (a) Tykwinski, R. R.; Stang, P. J. Organometallics 1994, 13, 3203. (b) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 923. (c) Lichtenberger, D. L.; Renshaw, S. K.; Bullock, R. M. J. Am. Chem. Soc. 1993, 115, 3276. (d) Lichtenberger, D. L.; Renshaw, S. K.; Wong, A.; Tagge, C. D. Organometallics 1993, 12, 3522. (e) Khan, M. S.; Davies, S. J.; Kakkar, A. K.; Schwartz, D.; Lin, B.; Johnson, B. F. G.; Lewis, J. J. Organomet. Chem. 1992, 424, 87. (f) Lewis, J.; Khan, M. S.; Kakkar, A. K.; Johnson, B. F. G.; Marder, T. B.; Fyfe, H. B.; Wittmann, F.; Friend, R. H.; Dray, A. E. J. Organomet. Chem. 1992, 425, 165.
29. Chemical Abstracts Service names compound 2 as [1,2-phenylenebis[(1,3-butadiyne-1,4-diyl-2,1-phenylene-2,1-ethynediyl)] bis(triethylphosphine)platinum. In lieu of this complicated name, we feel that describing 2 as an annulene derivative is more straightforward. Using this classification, molecule 2 would thus be a 5-platina-3,4,6,7,10,-11,12,13,16,17,18,19-dodecadehydro-1:2,8:9,14:15- tribenzo[19]annulene bis(triethylphosphine) complex, a name easily shortened to "platinadehydrobenzo[19]annulene".
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32. pt-P = 2344 Hz).
33. W = 0.045.
34. PM3 (tm) calculations were performed on a SGI workstation using Spartan molecular modeling software (Version 4.1.1). The calculations were done on the corresponding Pd complex of 2 as the program does not possess parameters for Pt. Nevertheless, due to the similarities between the two metals, all of the geometrical distortions (bent acetylenes, nonplanar annulene, tilt of phosphines) were duplicated with a very good degree of accuracy. A vast majority of the calculated bond lengths differed by less than 0.02 Å from the crystallographically observed values, and bond angles, by less than 1-2°.
35. Boese, R.; Matzger, A. J.; Mohler, D. L.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1478.