(R2PC2H4PR2)Pd 0-1-alkyne complexes

Organometallics

Volumn 16, Issue 20, 1997, Pages 4276-4286

  Schager, Frank ^a   Bonrath, Werner ^a   Pörschke, Klaus Richard ^a   Kessler, Magnus ^a   Krüger, Carl ^a   Seevogel, Klaus ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000869048     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9702035     Document Type: Article

References (91)

1. (a) Chukhadzhyan, G. A.; Évoyan, Z. K.; Melkonyan, L. N. Zh. Obshch. Khim. 1975, 45, 1114; J. Gen. Chem. USSR (Engl. Transl.) 1975, 45, 1096.
2. (a) Chukhadzhyan, G. A.; Évoyan, Z. K.; Melkonyan, L. N. Zh. Obshch. Khim. 1975, 45, 1114; J. Gen. Chem. USSR (Engl. Transl.) 1975, 45, 1096.
3. (b) Maitlis, P. M.; Espinet, F.; Russell, M. J. H. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982; Vol. 6, p 254.
4. (c) Davies, J. A. Comprehensive Organometallic Chemistry II; Pergamon: Oxford, U.K., 1995; Vol. 9, p 316.
5. Krause, J.; Bonrath, W.; Pörschke, K.-R. Organometallics 1992, 11, 1158.
6. Krause, J. Dissertation, Universität Düsseldorf, 1993.
7. 3 Goddard, R.; Krause, J.; Pörschke, K.-R. Unpublished results.
8. For IR spectroscopically characterized species obtained by cocondensation of Pd atoms and 1-alkynes, see: Zoellner, R. W.; Mabunde, K. J. Chem. Rev, 1984, 84, 545 and literature cited therein.
9. (a) Schager, F. Diplomarbeit, Universität Düsseldorf, 1995.
10. (b) Schager, F.; Pörschke, K.-R. GECOM-CONCOORD 1995, University of Rennes, May 28-June 1, 1995; St Jacut de la Mer, France,
11. (c) Schager, F. Planned Dissertation (1997).
12. 2(PhC≡CH) (unknown structure): Herrera, A.; Hoberg, H.; Mynott, R. J. Organomet. Chem. 1981, 222, 331.
13. 2Ni(PhC≡CH): Pörschke, K.-R.; Mynott, R.; Angermund, K.; Krüger, C. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1985, 40, 199.
14. 2Ni(PhC≡CH): Pörschke, K.-R.; Tsay, Y.-H.; Krüger, C. Angew. Chem. 1985, 97, 334; Angew. Chem., Int. Ed. Engl. 1985, 24, 323. Rosenthal, U.; Schulz, W. J. Organomet. Chem. 1987, 321, 103. Bartik, T.; Happ, B.; Iglewsky, M.; Bandmann, H.; Boese, R.; Heimbach, P.; Hoffmann, T.; Wenschuh, E. Organometallics 1992, 11, 1235.
15. 2Ni(PhC≡CH): Pörschke, K.-R.; Tsay, Y.-H.; Krüger, C. Angew. Chem. 1985, 97, 334; Angew. Chem., Int. Ed. Engl. 1985, 24, 323. Rosenthal, U.; Schulz, W. J. Organomet. Chem. 1987, 321, 103. Bartik, T.; Happ, B.; Iglewsky, M.; Bandmann, H.; Boese, R.; Heimbach, P.; Hoffmann, T.; Wenschuh, E. Organometallics 1992, 11, 1235.
16. 2Ni(PhC≡CH): Pörschke, K.-R.; Tsay, Y.-H.; Krüger, C. Angew. Chem. 1985, 97, 334; Angew. Chem., Int. Ed. Engl. 1985, 24, 323. Rosenthal, U.; Schulz, W. J. Organomet. Chem. 1987, 321, 103. Bartik, T.; Happ, B.; Iglewsky, M.; Bandmann, H.; Boese, R.; Heimbach, P.; Hoffmann, T.; Wenschuh, E. Organometallics 1992, 11, 1235.
17. 2Ni(PhC≡CH): Pörschke, K.-R.; Tsay, Y.-H.; Krüger, C. Angew. Chem. 1985, 97, 334; Angew. Chem., Int. Ed. Engl. 1985, 24, 323. Rosenthal, U.; Schulz, W. J. Organomet. Chem. 1987, 321, 103. Bartik, T.; Happ, B.; Iglewsky, M.; Bandmann, H.; Boese, R.; Heimbach, P.; Hoffmann, T.; Wenschuh, E. Organometallics 1992, 11, 1235.
18. (d) Chetcuti, M. J. Comprehensive Organometallic Chemistry II; Pergamon: Oxford, U.K., 1995; Vol. 9, p 129.
19. Selected references: (a) Allen, A. D.; Cook, C. D. Can. J. Chem. 1964, 42, 1063. Harbourne, D. A.; Stone, F. G. A. J. Chem. Soc. A 1968, 1765. Nelson, J. H.; Jonassen, H. B.; Roundhill, D. M. Inorg. Chem. 1969, 8, 2591. Tripathy, P. B.; Roundhill, D. M. J. Organomet. Chem. 1970, 24, 247. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667. Furlani, A.; Carusi, P.; Russo, M. V. J. Organomet. Chem. 1974, 67, 315. Empsall, H. D.; Shaw, B. L. Stringer, A. J. J. Chem. Soc., Dalton Trans. 1976, 185. Jagner, S.; Hazell, R. G.; Rasmussen, S. E. J. Chem. Soc., Dalton Trans. 1976, 337. Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1981, 210, 403. (b) Hartley, F. R. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982; Vol. 6, p 691. Young, G. B. Comprehensive Organometallic Chemistry II; Pergamon: Oxford, U.K., 1995; Vol. 9, p 564.
20. Selected references: (a) Allen, A. D.; Cook, C. D. Can. J. Chem. 1964, 42, 1063. Harbourne, D. A.; Stone, F. G. A. J. Chem. Soc. A 1968, 1765. Nelson, J. H.; Jonassen, H. B.; Roundhill, D. M. Inorg. Chem. 1969, 8, 2591. Tripathy, P. B.; Roundhill, D. M. J. Organomet. Chem. 1970, 24, 247. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667. Furlani, A.; Carusi, P.; Russo, M. V. J. Organomet. Chem. 1974, 67, 315. Empsall, H. D.; Shaw, B. L. Stringer, A. J. J. Chem. Soc., Dalton Trans. 1976, 185. Jagner, S.; Hazell, R. G.; Rasmussen, S. E. J. Chem. Soc., Dalton Trans. 1976, 337. Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1981, 210, 403. (b) Hartley, F. R. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982; Vol. 6, p 691. Young, G. B. Comprehensive Organometallic Chemistry II; Pergamon: Oxford, U.K., 1995; Vol. 9, p 564.
21. Selected references: (a) Allen, A. D.; Cook, C. D. Can. J. Chem. 1964, 42, 1063. Harbourne, D. A.; Stone, F. G. A. J. Chem. Soc. A 1968, 1765. Nelson, J. H.; Jonassen, H. B.; Roundhill, D. M. Inorg. Chem. 1969, 8, 2591. Tripathy, P. B.; Roundhill, D. M. J. Organomet. Chem. 1970, 24, 247. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667. Furlani, A.; Carusi, P.; Russo, M. V. J. Organomet. Chem. 1974, 67, 315. Empsall, H. D.; Shaw, B. L. Stringer, A. J. J. Chem. Soc., Dalton Trans. 1976, 185. Jagner, S.; Hazell, R. G.; Rasmussen, S. E. J. Chem. Soc., Dalton Trans. 1976, 337. Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1981, 210, 403. (b) Hartley, F. R. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982; Vol. 6, p 691. Young, G. B. Comprehensive Organometallic Chemistry II; Pergamon: Oxford, U.K., 1995; Vol. 9, p 564.
22. Selected references: (a) Allen, A. D.; Cook, C. D. Can. J. Chem. 1964, 42, 1063. Harbourne, D. A.; Stone, F. G. A. J. Chem. Soc. A 1968, 1765. Nelson, J. H.; Jonassen, H. B.; Roundhill, D. M. Inorg. Chem. 1969, 8, 2591. Tripathy, P. B.; Roundhill, D. M. J. Organomet. Chem. 1970, 24, 247. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667. Furlani, A.; Carusi, P.; Russo, M. V. J. Organomet. Chem. 1974, 67, 315. Empsall, H. D.; Shaw, B. L. Stringer, A. J. J. Chem. Soc., Dalton Trans. 1976, 185. Jagner, S.; Hazell, R. G.; Rasmussen, S. E. J. Chem. Soc., Dalton Trans. 1976, 337. Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1981, 210, 403. (b) Hartley, F. R. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982; Vol. 6, p 691. Young, G. B. Comprehensive Organometallic Chemistry II; Pergamon: Oxford, U.K., 1995; Vol. 9, p 564.
23. Selected references: (a) Allen, A. D.; Cook, C. D. Can. J. Chem. 1964, 42, 1063. Harbourne, D. A.; Stone, F. G. A. J. Chem. Soc. A 1968, 1765. Nelson, J. H.; Jonassen, H. B.; Roundhill, D. M. Inorg. Chem. 1969, 8, 2591. Tripathy, P. B.; Roundhill, D. M. J. Organomet. Chem. 1970, 24, 247. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667. Furlani, A.; Carusi, P.; Russo, M. V. J. Organomet. Chem. 1974, 67, 315. Empsall, H. D.; Shaw, B. L. Stringer, A. J. J. Chem. Soc., Dalton Trans. 1976, 185. Jagner, S.; Hazell, R. G.; Rasmussen, S. E. J. Chem. Soc., Dalton Trans. 1976, 337. Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1981, 210, 403. (b) Hartley, F. R. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982; Vol. 6, p 691. Young, G. B. Comprehensive Organometallic Chemistry II; Pergamon: Oxford, U.K., 1995; Vol. 9, p 564.
24. Selected references: (a) Allen, A. D.; Cook, C. D. Can. J. Chem. 1964, 42, 1063. Harbourne, D. A.; Stone, F. G. A. J. Chem. Soc. A 1968, 1765. Nelson, J. H.; Jonassen, H. B.; Roundhill, D. M. Inorg. Chem. 1969, 8, 2591. Tripathy, P. B.; Roundhill, D. M. J. Organomet. Chem. 1970, 24, 247. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667. Furlani, A.; Carusi, P.; Russo, M. V. J. Organomet. Chem. 1974, 67, 315. Empsall, H. D.; Shaw, B. L. Stringer, A. J. J. Chem. Soc., Dalton Trans. 1976, 185. Jagner, S.; Hazell, R. G.; Rasmussen, S. E. J. Chem. Soc., Dalton Trans. 1976, 337. Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1981, 210, 403. (b) Hartley, F. R. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982; Vol. 6, p 691. Young, G. B. Comprehensive Organometallic Chemistry II; Pergamon: Oxford, U.K., 1995; Vol. 9, p 564.
25. Selected references: (a) Allen, A. D.; Cook, C. D. Can. J. Chem. 1964, 42, 1063. Harbourne, D. A.; Stone, F. G. A. J. Chem. Soc. A 1968, 1765. Nelson, J. H.; Jonassen, H. B.; Roundhill, D. M. Inorg. Chem. 1969, 8, 2591. Tripathy, P. B.; Roundhill, D. M. J. Organomet. Chem. 1970, 24, 247. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667. Furlani, A.; Carusi, P.; Russo, M. V. J. Organomet. Chem. 1974, 67, 315. Empsall, H. D.; Shaw, B. L. Stringer, A. J. J. Chem. Soc., Dalton Trans. 1976, 185. Jagner, S.; Hazell, R. G.; Rasmussen, S. E. J. Chem. Soc., Dalton Trans. 1976, 337. Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1981, 210, 403. (b) Hartley, F. R. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982; Vol. 6, p 691. Young, G. B. Comprehensive Organometallic Chemistry II; Pergamon: Oxford, U.K., 1995; Vol. 9, p 564.
26. Selected references: (a) Allen, A. D.; Cook, C. D. Can. J. Chem. 1964, 42, 1063. Harbourne, D. A.; Stone, F. G. A. J. Chem. Soc. A 1968, 1765. Nelson, J. H.; Jonassen, H. B.; Roundhill, D. M. Inorg. Chem. 1969, 8, 2591. Tripathy, P. B.; Roundhill, D. M. J. Organomet. Chem. 1970, 24, 247. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667. Furlani, A.; Carusi, P.; Russo, M. V. J. Organomet. Chem. 1974, 67, 315. Empsall, H. D.; Shaw, B. L. Stringer, A. J. J. Chem. Soc., Dalton Trans. 1976, 185. Jagner, S.; Hazell, R. G.; Rasmussen, S. E. J. Chem. Soc., Dalton Trans. 1976, 337. Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1981, 210, 403. (b) Hartley, F. R. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982; Vol. 6, p 691. Young, G. B. Comprehensive Organometallic Chemistry II; Pergamon: Oxford, U.K., 1995; Vol. 9, p 564.
27. Selected references: (a) Allen, A. D.; Cook, C. D. Can. J. Chem. 1964, 42, 1063. Harbourne, D. A.; Stone, F. G. A. J. Chem. Soc. A 1968, 1765. Nelson, J. H.; Jonassen, H. B.; Roundhill, D. M. Inorg. Chem. 1969, 8, 2591. Tripathy, P. B.; Roundhill, D. M. J. Organomet. Chem. 1970, 24, 247. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667. Furlani, A.; Carusi, P.; Russo, M. V. J. Organomet. Chem. 1974, 67, 315. Empsall, H. D.; Shaw, B. L. Stringer, A. J. J. Chem. Soc., Dalton Trans. 1976, 185. Jagner, S.; Hazell, R. G.; Rasmussen, S. E. J. Chem. Soc., Dalton Trans. 1976, 337. Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1981, 210, 403. (b) Hartley, F. R. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982; Vol. 6, p 691. Young, G. B. Comprehensive Organometallic Chemistry II; Pergamon: Oxford, U.K., 1995; Vol. 9, p 564.
28. Selected references: (a) Allen, A. D.; Cook, C. D. Can. J. Chem. 1964, 42, 1063. Harbourne, D. A.; Stone, F. G. A. J. Chem. Soc. A 1968, 1765. Nelson, J. H.; Jonassen, H. B.; Roundhill, D. M. Inorg. Chem. 1969, 8, 2591. Tripathy, P. B.; Roundhill, D. M. J. Organomet. Chem. 1970, 24, 247. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667. Furlani, A.; Carusi, P.; Russo, M. V. J. Organomet. Chem. 1974, 67, 315. Empsall, H. D.; Shaw, B. L. Stringer, A. J. J. Chem. Soc., Dalton Trans. 1976, 185. Jagner, S.; Hazell, R. G.; Rasmussen, S. E. J. Chem. Soc., Dalton Trans. 1976, 337. Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1981, 210, 403. (b) Hartley, F. R. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982; Vol. 6, p 691. Young, G. B. Comprehensive Organometallic Chemistry II; Pergamon: Oxford, U.K., 1995; Vol. 9, p 564.
29. Selected references: (a) Allen, A. D.; Cook, C. D. Can. J. Chem. 1964, 42, 1063. Harbourne, D. A.; Stone, F. G. A. J. Chem. Soc. A 1968, 1765. Nelson, J. H.; Jonassen, H. B.; Roundhill, D. M. Inorg. Chem. 1969, 8, 2591. Tripathy, P. B.; Roundhill, D. M. J. Organomet. Chem. 1970, 24, 247. Mann, B. E.; Shaw, B. L.; Tucker, N. I. J. Chem. Soc. A 1971, 2667. Furlani, A.; Carusi, P.; Russo, M. V. J. Organomet. Chem. 1974, 67, 315. Empsall, H. D.; Shaw, B. L. Stringer, A. J. J. Chem. Soc., Dalton Trans. 1976, 185. Jagner, S.; Hazell, R. G.; Rasmussen, S. E. J. Chem. Soc., Dalton Trans. 1976, 337. Butler, G.; Eaborn, C.; Pidcock, A. J. Organomet. Chem. 1981, 210, 403. (b) Hartley, F. R. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982; Vol. 6, p 691. Young, G. B. Comprehensive Organometallic Chemistry II; Pergamon: Oxford, U.K., 1995; Vol. 9, p 564.
30. For examples of Pd-catalyzed oligo- or polymerization of terminal alkynes, see: (a) Odaira, Y.; Hara, M.; Tsutsumi, S. Technol. Rep. Osaka Univ. 1965, 16, 325; Chem. Abstr. 1966, 65,10670f. (b) Maitlis, P. M. Acc. Chem. Res. 1976, 9, 93 and references cited therein. (c) Simionescu, C. I.; Percee, V.; Dumitrescu, S. J. Polym. Sci., Polym. Chem. Ed. 1977, 15, 2497. (d) Sabourin, E. T. J. Mol. Catal. 1984, 26, 363. (e) Ishikawa, M.; Ohshita, J.; Ito, Y.; Minato, A. J. Organomet. Chem. 1988, 346, C58. (f) Dzhemilev, U. M.; Khusnutdinov, R. I.; Shchadneva, N. A.; Nefedov, O. M.; Tolstikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 2360; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 2171. (g) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rünter, G. J. Am. Chem. Soc. 1997, 119, 698.
31. For examples of Pd-catalyzed oligo- or polymerization of terminal alkynes, see: (a) Odaira, Y.; Hara, M.; Tsutsumi, S. Technol. Rep. Osaka Univ. 1965, 16, 325; Chem. Abstr. 1966, 65,10670f. (b) Maitlis, P. M. Acc. Chem. Res. 1976, 9, 93 and references cited therein. (c) Simionescu, C. I.; Percee, V.; Dumitrescu, S. J. Polym. Sci., Polym. Chem. Ed. 1977, 15, 2497. (d) Sabourin, E. T. J. Mol. Catal. 1984, 26, 363. (e) Ishikawa, M.; Ohshita, J.; Ito, Y.; Minato, A. J. Organomet. Chem. 1988, 346, C58. (f) Dzhemilev, U. M.; Khusnutdinov, R. I.; Shchadneva, N. A.; Nefedov, O. M.; Tolstikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 2360; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 2171. (g) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rünter, G. J. Am. Chem. Soc. 1997, 119, 698.
32. For examples of Pd-catalyzed oligo- or polymerization of terminal alkynes, see: (a) Odaira, Y.; Hara, M.; Tsutsumi, S. Technol. Rep. Osaka Univ. 1965, 16, 325; Chem. Abstr. 1966, 65,10670f. (b) Maitlis, P. M. Acc. Chem. Res. 1976, 9, 93 and references cited therein. (c) Simionescu, C. I.; Percee, V.; Dumitrescu, S. J. Polym. Sci., Polym. Chem. Ed. 1977, 15, 2497. (d) Sabourin, E. T. J. Mol. Catal. 1984, 26, 363. (e) Ishikawa, M.; Ohshita, J.; Ito, Y.; Minato, A. J. Organomet. Chem. 1988, 346, C58. (f) Dzhemilev, U. M.; Khusnutdinov, R. I.; Shchadneva, N. A.; Nefedov, O. M.; Tolstikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 2360; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 2171. (g) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rünter, G. J. Am. Chem. Soc. 1997, 119, 698.
33. For examples of Pd-catalyzed oligo- or polymerization of terminal alkynes, see: (a) Odaira, Y.; Hara, M.; Tsutsumi, S. Technol. Rep. Osaka Univ. 1965, 16, 325; Chem. Abstr. 1966, 65,10670f. (b) Maitlis, P. M. Acc. Chem. Res. 1976, 9, 93 and references cited therein. (c) Simionescu, C. I.; Percee, V.; Dumitrescu, S. J. Polym. Sci., Polym. Chem. Ed. 1977, 15, 2497. (d) Sabourin, E. T. J. Mol. Catal. 1984, 26, 363. (e) Ishikawa, M.; Ohshita, J.; Ito, Y.; Minato, A. J. Organomet. Chem. 1988, 346, C58. (f) Dzhemilev, U. M.; Khusnutdinov, R. I.; Shchadneva, N. A.; Nefedov, O. M.; Tolstikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 2360; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 2171. (g) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rünter, G. J. Am. Chem. Soc. 1997, 119, 698.
34. For examples of Pd-catalyzed oligo- or polymerization of terminal alkynes, see: (a) Odaira, Y.; Hara, M.; Tsutsumi, S. Technol. Rep. Osaka Univ. 1965, 16, 325; Chem. Abstr. 1966, 65,10670f. (b) Maitlis, P. M. Acc. Chem. Res. 1976, 9, 93 and references cited therein. (c) Simionescu, C. I.; Percee, V.; Dumitrescu, S. J. Polym. Sci., Polym. Chem. Ed. 1977, 15, 2497. (d) Sabourin, E. T. J. Mol. Catal. 1984, 26, 363. (e) Ishikawa, M.; Ohshita, J.; Ito, Y.; Minato, A. J. Organomet. Chem. 1988, 346, C58. (f) Dzhemilev, U. M.; Khusnutdinov, R. I.; Shchadneva, N. A.; Nefedov, O. M.; Tolstikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 2360; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 2171. (g) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rünter, G. J. Am. Chem. Soc. 1997, 119, 698.
35. For examples of Pd-catalyzed oligo- or polymerization of terminal alkynes, see: (a) Odaira, Y.; Hara, M.; Tsutsumi, S. Technol. Rep. Osaka Univ. 1965, 16, 325; Chem. Abstr. 1966, 65,10670f. (b) Maitlis, P. M. Acc. Chem. Res. 1976, 9, 93 and references cited therein. (c) Simionescu, C. I.; Percee, V.; Dumitrescu, S. J. Polym. Sci., Polym. Chem. Ed. 1977, 15, 2497. (d) Sabourin, E. T. J. Mol. Catal. 1984, 26, 363. (e) Ishikawa, M.; Ohshita, J.; Ito, Y.; Minato, A. J. Organomet. Chem. 1988, 346, C58. (f) Dzhemilev, U. M.; Khusnutdinov, R. I.; Shchadneva, N. A.; Nefedov, O. M.; Tolstikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 2360; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 2171. (g) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rünter, G. J. Am. Chem. Soc. 1997, 119, 698.
36. For examples of Pd-catalyzed oligo- or polymerization of terminal alkynes, see: (a) Odaira, Y.; Hara, M.; Tsutsumi, S. Technol. Rep. Osaka Univ. 1965, 16, 325; Chem. Abstr. 1966, 65,10670f. (b) Maitlis, P. M. Acc. Chem. Res. 1976, 9, 93 and references cited therein. (c) Simionescu, C. I.; Percee, V.; Dumitrescu, S. J. Polym. Sci., Polym. Chem. Ed. 1977, 15, 2497. (d) Sabourin, E. T. J. Mol. Catal. 1984, 26, 363. (e) Ishikawa, M.; Ohshita, J.; Ito, Y.; Minato, A. J. Organomet. Chem. 1988, 346, C58. (f) Dzhemilev, U. M.; Khusnutdinov, R. I.; Shchadneva, N. A.; Nefedov, O. M.; Tolstikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 2360; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 2171. (g) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rünter, G. J. Am. Chem. Soc. 1997, 119, 698.
37. For examples of Pd-catalyzed oligo- or polymerization of terminal alkynes, see: (a) Odaira, Y.; Hara, M.; Tsutsumi, S. Technol. Rep. Osaka Univ. 1965, 16, 325; Chem. Abstr. 1966, 65,10670f. (b) Maitlis, P. M. Acc. Chem. Res. 1976, 9, 93 and references cited therein. (c) Simionescu, C. I.; Percee, V.; Dumitrescu, S. J. Polym. Sci., Polym. Chem. Ed. 1977, 15, 2497. (d) Sabourin, E. T. J. Mol. Catal. 1984, 26, 363. (e) Ishikawa, M.; Ohshita, J.; Ito, Y.; Minato, A. J. Organomet. Chem. 1988, 346, C58. (f) Dzhemilev, U. M.; Khusnutdinov, R. I.; Shchadneva, N. A.; Nefedov, O. M.; Tolstikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 2360; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 2171. (g) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rünter, G. J. Am. Chem. Soc. 1997, 119, 698.
38. For examples of Pd-catalyzed oligo- or polymerization of terminal alkynes, see: (a) Odaira, Y.; Hara, M.; Tsutsumi, S. Technol. Rep. Osaka Univ. 1965, 16, 325; Chem. Abstr. 1966, 65,10670f. (b) Maitlis, P. M. Acc. Chem. Res. 1976, 9, 93 and references cited therein. (c) Simionescu, C. I.; Percee, V.; Dumitrescu, S. J. Polym. Sci., Polym. Chem. Ed. 1977, 15, 2497. (d) Sabourin, E. T. J. Mol. Catal. 1984, 26, 363. (e) Ishikawa, M.; Ohshita, J.; Ito, Y.; Minato, A. J. Organomet. Chem. 1988, 346, C58. (f) Dzhemilev, U. M.; Khusnutdinov, R. I.; Shchadneva, N. A.; Nefedov, O. M.; Tolstikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 2360; Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1990, 2171. (g) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rünter, G. J. Am. Chem. Soc. 1997, 119, 698.
39. 3 Krause, J.; Schager, F.; Pörschke, K.-R. 32nd International Conference on Coordination Chemistry, Santiago, Chile, Aug 24-29, 1997.
40. 1H FT NMR Spectra; 1st ed.; Aldrich Chemical: Milwaukee, WI 1993; p 1282 (spectrum for 11,598-3).
41. (a) Krause, J.; Pluta, C.; Pörschke, K.-R.; Goddard, R. J. Chem. Soc., Chem. Commun. 1993, 1254.
42. (b) Krause, J.; Haack, K.-J.; Pörschke, K.-R.; Gabor, B.; Goddard, R.; Pluta, C.; Seevogel, K. J. Am. Chem. Soc. 1996, 118, 804.
43. (a) Goddard, R.; Hopp, G.; Jolly, P. W.; Krüger, C.; Mynott, R.; Wirtz, C. J. Organomet. Chem. 1995, 486, 163.
44. (b) Schager, F.; Seevogel, K.; Pörschke, K.-R.; Kessler, M.; Krüger, C. J. Am. Chem. Soc. 1996, 118, 13075.
45. (a) McGinnety, J. A. J. Chem. Soc., Dalton Trans. 1974, 1038.
46. (b) Farrar, D. H.; Payne, N. C. J. Organomet. Chem. 1981, 220, 239.
47. (a) Haack, K.-J. Dissertation, Universität Düsseldorf, 1994.
48. (b) Krüger, C.; Goddard, R. Unpublished results.
49. I radical ion character.
50. free alkyne. Thus, typical alkyne coordination shifts to lower field are positive, whereas those to higher field are negative. Jolly, P. W.; Mynott, R. Adv. Organomet. Chem, 1981, 19, 257.
51. 31P AB signals of 2a coalesce at 27 °C due to the very small difference in chemical shifts.
52. (a) Benn, R.; Jolly, P. W.; Joswig, T.; Mynott, R.; Schick, K.-P. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1986, 41, 680.
53. (b) Topalovic, I. Dissertation, Universität Siegen, 1990.
54. (c) Benn, R.; Betz, P.; Goddard, R.; Jolly, P. W.; Kokel, N.; Krüger, C.; Topalovic, I. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1991, 46, 1395.
55. Bonrath, W.; Pörschke, K.-R.; Wilke, G.; Angermund, K; Krüger, C. Angew. Chem. 1988, 100, 853; Angew. Chem., Int. Ed. Engl. 1988, 27, 833.
56. Bonrath, W.; Pörschke, K.-R.; Wilke, G.; Angermund, K; Krüger, C. Angew. Chem. 1988, 100, 853; Angew. Chem., Int. Ed. Engl. 1988, 27, 833.
57. Bonrath, W. Dissertation, Universität Bochum, 1988.
58. 15a
59. 2) appears to be unstable. Cestaric, G. Diplomarbeit, Universität Düsseldorf, 1996.
60. 2) appears to be unstable. Cestaric, G. Diplomarbeit, Universität Düsseldorf, 1996.
61. 2) appears to be unstable. Cestaric, G. Diplomarbeit, Universität Düsseldorf, 1996.
62. 2) appears to be unstable. Cestaric, G. Diplomarbeit, Universität Düsseldorf, 1996.
63. 2) appears to be unstable. Cestaric, G. Diplomarbeit, Universität Düsseldorf, 1996.
64. 2) appears to be unstable. Cestaric, G. Diplomarbeit, Universität Düsseldorf, 1996.
65. 2) appears to be unstable. Cestaric, G. Diplomarbeit, Universität Düsseldorf, 1996.
66. 2) appears to be unstable. Cestaric, G. Diplomarbeit, Universität Düsseldorf, 1996.
67. 2) appears to be unstable. Cestaric, G. Diplomarbeit, Universität Düsseldorf, 1996.
68. (a) Farrar, D. H.; Payne, N. C. J. Organomet. Chem. 1981, 220, 251.
69. (b) Rosenthal, U.; Oehme, G.; Görls, H.; Burlakov, V. V.; Polyakov, A. V.; Yanovsky, A. I.; Struchkov, Y. T. J. Organomet. Chem. 1990, 389, 251.
70. Without question dinuclear derivatives of 9-11 can also be prepared by applying a procedure similar to that for 8b, although this has not been attempted by us.
71. r = 737.6) has been encountered before by various groups,
72. (a) Hopp, G.; Jolly, P. W.; Krause, J.; Pörschke, K.-R. Unpublished results,
73. 15a
74. (c) Fryzuk, M. D.; Clentsmith, G. K, B.; Rettig, S. J.; Hägele, G. Organometallics 1996, 15, 2083.
75. Pan, Y.; Mague, J. T.; Fink, M. J. J. Am. Chem. Soc. 1993, 115, 3842. Landtiser, R.; Pan, Y.; Fink, M. J. Phosphorus, Sulfur Silicon Relat. Eiern. 1994, 93-94, 393.
76. Pan, Y.; Mague, J. T.; Fink, M. J. J. Am. Chem. Soc. 1993, 115, 3842. Landtiser, R.; Pan, Y.; Fink, M. J. Phosphorus, Sulfur Silicon Relat. Eiern. 1994, 93-94, 393.
77. H 3.88). Diercks, R.; tom Dieck, H. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1984, 39, 180.
78. (a) Charton, M. Prog. Phys. Org. Chem. 1981, 73, 119.
79. 2)}/2, respectively.
80. (a) Herberich, G. E.; Okuda, J. Chem. Ber. 1984, 117, 3112.
81. (b) Rosenthal, U.; Schulz, W. J. Organomet. Chem. 1987, 321, 103. Rosenthal, U.; Oehme, G.; Burlakov, V. V.; Petrovskii, P. V.; Shur, V. B.; Vol'pin, M. E. J. Organomet. Chem. 1990, 397, 119.
82. (b) Rosenthal, U.; Schulz, W. J. Organomet. Chem. 1987, 321, 103. Rosenthal, U.; Oehme, G.; Burlakov, V. V.; Petrovskii, P. V.; Shur, V. B.; Vol'pin, M. E. J. Organomet. Chem. 1990, 397, 119.
83. 3
84. See ref 2 and literature cited therein.
85. (a) Müller, J.; Göser, P. Angew. Chem. 1967, 79, 380; Angew. Chem., Int. Ed. Engl. 1967, 6, 364.
86. (a) Müller, J.; Göser, P. Angew. Chem. 1967, 79, 380; Angew. Chem., Int. Ed. Engl. 1967, 6, 364.
87. (b) Green, M.; Howard, J. A. K.; Spencer, J. L.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1977, 271.
88. (c) Herberich, G. E.; Hessner, B. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1979, 34, 638.
89. (d) Crascall, L. E.; Spencer, J. L. Inorg. Synth. 1990, 28, 126.
90. Sheldrick, G. M. SHELXS-86. Acta Crystallogr., Sect. A 1990, 46, 467.
91. Sheldrick, G. M. SHELXL-93, Program for Crystal Structure Refinement; Universität Göttingen: Göttingen, Germany, 1993.