A novel route to functionalized terminal alkynes through η1-vinylidene to η2-alkyne tautomerizations in indenyl-ruthenium(II) monosubstituted vinylidene complexes: Synthetic and theoretical studies

Organometallics

Volumn 18, Issue 15, 1999, Pages 2821-2832

  Cadierno, Victorio ^a   Gamasa, M Pilar ^a   Gimeno, José ^a   Pérez Carreño, Enrique ^a   García Granda, Santiago ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000859926     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990194v     Document Type: Article

References (94)

1. For comprehensive reviews see: (a) Bruce, M. I. Chem. Rev. 1991, 91, 197; 1998, 98, 2797. (b) Antonova, A. B.; Ioganson, A. A. Russ. Chem. Rev. (Engl. Transl.) 1989, 58, 693. (c) Werner, H. J. Organomet. Chem. 1994, 475, 45.
2. For comprehensive reviews see: (a) Bruce, M. I. Chem. Rev. 1991, 91, 197; 1998, 98, 2797. (b) Antonova, A. B.; Ioganson, A. A. Russ. Chem. Rev. (Engl. Transl.) 1989, 58, 693. (c) Werner, H. J. Organomet. Chem. 1994, 475, 45.
3. For comprehensive reviews see: (a) Bruce, M. I. Chem. Rev. 1991, 91, 197; 1998, 98, 2797. (b) Antonova, A. B.; Ioganson, A. A. Russ. Chem. Rev. (Engl. Transl.) 1989, 58, 693. (c) Werner, H. J. Organomet. Chem. 1994, 475, 45.
4. For comprehensive reviews see: (a) Bruce, M. I. Chem. Rev. 1991, 91, 197; 1998, 98, 2797. (b) Antonova, A. B.; Ioganson, A. A. Russ. Chem. Rev. (Engl. Transl.) 1989, 58, 693. (c) Werner, H. J. Organomet. Chem. 1994, 475, 45.
5. See for example: (a) Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Organomet. Chem. 1990, 30, 1, and references therein. (b) Bianchini, C.; Glendenning, L.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Chem. Soc., Chem. Commun. 1994, 2219. (c) Bianchini, C.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1995, 14, 3152. (d) Nombel, P.; Lugan, N.; Mathieu, R. J. Organomet. Chem. 1995, 503, C22. (e) Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585, and references therein. (f) Chang, K. H.; Lin, Y. C. Chem. Commun. 1998, 1441. (g) Yam, V. W.-W.; Chu, B. W.-K.; Cheung, K.-K. Chem. Commun. 1998, 2261.
6. See for example: (a) Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Organomet. Chem. 1990, 30, 1, and references therein. (b) Bianchini, C.; Glendenning, L.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Chem. Soc., Chem. Commun. 1994, 2219. (c) Bianchini, C.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1995, 14, 3152. (d) Nombel, P.; Lugan, N.; Mathieu, R. J. Organomet. Chem. 1995, 503, C22. (e) Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585, and references therein. (f) Chang, K. H.; Lin, Y. C. Chem. Commun. 1998, 1441. (g) Yam, V. W.-W.; Chu, B. W.-K.; Cheung, K.-K. Chem. Commun. 1998, 2261.
7. See for example: (a) Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Organomet. Chem. 1990, 30, 1, and references therein. (b) Bianchini, C.; Glendenning, L.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Chem. Soc., Chem. Commun. 1994, 2219. (c) Bianchini, C.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1995, 14, 3152. (d) Nombel, P.; Lugan, N.; Mathieu, R. J. Organomet. Chem. 1995, 503, C22. (e) Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585, and references therein. (f) Chang, K. H.; Lin, Y. C. Chem. Commun. 1998, 1441. (g) Yam, V. W.-W.; Chu, B. W.-K.; Cheung, K.-K. Chem. Commun. 1998, 2261.
8. See for example: (a) Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Organomet. Chem. 1990, 30, 1, and references therein. (b) Bianchini, C.; Glendenning, L.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Chem. Soc., Chem. Commun. 1994, 2219. (c) Bianchini, C.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1995, 14, 3152. (d) Nombel, P.; Lugan, N.; Mathieu, R. J. Organomet. Chem. 1995, 503, C22. (e) Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585, and references therein. (f) Chang, K. H.; Lin, Y. C. Chem. Commun. 1998, 1441. (g) Yam, V. W.-W.; Chu, B. W.-K.; Cheung, K.-K. Chem. Commun. 1998, 2261.
9. See for example: (a) Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Organomet. Chem. 1990, 30, 1, and references therein. (b) Bianchini, C.; Glendenning, L.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Chem. Soc., Chem. Commun. 1994, 2219. (c) Bianchini, C.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1995, 14, 3152. (d) Nombel, P.; Lugan, N.; Mathieu, R. J. Organomet. Chem. 1995, 503, C22. (e) Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585, and references therein. (f) Chang, K. H.; Lin, Y. C. Chem. Commun. 1998, 1441. (g) Yam, V. W.-W.; Chu, B. W.-K.; Cheung, K.-K. Chem. Commun. 1998, 2261.
10. See for example: (a) Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Organomet. Chem. 1990, 30, 1, and references therein. (b) Bianchini, C.; Glendenning, L.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Chem. Soc., Chem. Commun. 1994, 2219. (c) Bianchini, C.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1995, 14, 3152. (d) Nombel, P.; Lugan, N.; Mathieu, R. J. Organomet. Chem. 1995, 503, C22. (e) Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585, and references therein. (f) Chang, K. H.; Lin, Y. C. Chem. Commun. 1998, 1441. (g) Yam, V. W.-W.; Chu, B. W.-K.; Cheung, K.-K. Chem. Commun. 1998, 2261.
11. See for example: (a) Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Organomet. Chem. 1990, 30, 1, and references therein. (b) Bianchini, C.; Glendenning, L.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Chem. Soc., Chem. Commun. 1994, 2219. (c) Bianchini, C.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1995, 14, 3152. (d) Nombel, P.; Lugan, N.; Mathieu, R. J. Organomet. Chem. 1995, 503, C22. (e) Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585, and references therein. (f) Chang, K. H.; Lin, Y. C. Chem. Commun. 1998, 1441. (g) Yam, V. W.-W.; Chu, B. W.-K.; Cheung, K.-K. Chem. Commun. 1998, 2261.
12. For recent references see: (a) Albertin, G.; Antoniutti, S.; Bordignon, E.; Cazzaro, F.; Ianelli, S.; Pellizi, G. Organometallics 1995, 14, 4114. (b) Wang, Y.; Finn, M. G. J. Am. Chem. Soc. 1995, 117, 8045. (c) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (d) Braun, T.; Meuer, P.; Werner, H. Organometallics 1996, 15, 4075. (e) Ting, P. C.; Lin, Y. C.; Lee, G. H.; Cheng, M. C.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 6433. (f) Yang, S. M.; Chan, M. C. W.; Cheung, K. K.; Che, C. M.; Peng, S. M. Organometallics 1997, 16, 2819. (g) Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Am. Chem. Soc. 1998, 120, 6175. (h) Jia, G.; Lau, C. P. J. Organomet. Chem. 1998, 565, 37, and references therein. (i) Slugovc, C.; Mauthner, K.; Kacetl, M.; Mereiter, K.; Schmid, R.; Kirchner, K. Chem. Eur. J. 1998, 4, 2043. (j) Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158 (k) Huang, D.; Oliván, M.; Huffman, J. C.; Eisenstein, O.; Caulton, K G. Organometallics 1998, 17, 4700.
13. For recent references see: (a) Albertin, G.; Antoniutti, S.; Bordignon, E.; Cazzaro, F.; Ianelli, S.; Pellizi, G. Organometallics 1995, 14, 4114. (b) Wang, Y.; Finn, M. G. J. Am. Chem. Soc. 1995, 117, 8045. (c) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (d) Braun, T.; Meuer, P.; Werner, H. Organometallics 1996, 15, 4075. (e) Ting, P. C.; Lin, Y. C.; Lee, G. H.; Cheng, M. C.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 6433. (f) Yang, S. M.; Chan, M. C. W.; Cheung, K. K.; Che, C. M.; Peng, S. M. Organometallics 1997, 16, 2819. (g) Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Am. Chem. Soc. 1998, 120, 6175. (h) Jia, G.; Lau, C. P. J. Organomet. Chem. 1998, 565, 37, and references therein. (i) Slugovc, C.; Mauthner, K.; Kacetl, M.; Mereiter, K.; Schmid, R.; Kirchner, K. Chem. Eur. J. 1998, 4, 2043. (j) Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158 (k) Huang, D.; Oliván, M.; Huffman, J. C.; Eisenstein, O.; Caulton, K G. Organometallics 1998, 17, 4700.
14. For recent references see: (a) Albertin, G.; Antoniutti, S.; Bordignon, E.; Cazzaro, F.; Ianelli, S.; Pellizi, G. Organometallics 1995, 14, 4114. (b) Wang, Y.; Finn, M. G. J. Am. Chem. Soc. 1995, 117, 8045. (c) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (d) Braun, T.; Meuer, P.; Werner, H. Organometallics 1996, 15, 4075. (e) Ting, P. C.; Lin, Y. C.; Lee, G. H.; Cheng, M. C.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 6433. (f) Yang, S. M.; Chan, M. C. W.; Cheung, K. K.; Che, C. M.; Peng, S. M. Organometallics 1997, 16, 2819. (g) Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Am. Chem. Soc. 1998, 120, 6175. (h) Jia, G.; Lau, C. P. J. Organomet. Chem. 1998, 565, 37, and references therein. (i) Slugovc, C.; Mauthner, K.; Kacetl, M.; Mereiter, K.; Schmid, R.; Kirchner, K. Chem. Eur. J. 1998, 4, 2043. (j) Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158 (k) Huang, D.; Oliván, M.; Huffman, J. C.; Eisenstein, O.; Caulton, K G. Organometallics 1998, 17, 4700.
15. For recent references see: (a) Albertin, G.; Antoniutti, S.; Bordignon, E.; Cazzaro, F.; Ianelli, S.; Pellizi, G. Organometallics 1995, 14, 4114. (b) Wang, Y.; Finn, M. G. J. Am. Chem. Soc. 1995, 117, 8045. (c) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (d) Braun, T.; Meuer, P.; Werner, H. Organometallics 1996, 15, 4075. (e) Ting, P. C.; Lin, Y. C.; Lee, G. H.; Cheng, M. C.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 6433. (f) Yang, S. M.; Chan, M. C. W.; Cheung, K. K.; Che, C. M.; Peng, S. M. Organometallics 1997, 16, 2819. (g) Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Am. Chem. Soc. 1998, 120, 6175. (h) Jia, G.; Lau, C. P. J. Organomet. Chem. 1998, 565, 37, and references therein. (i) Slugovc, C.; Mauthner, K.; Kacetl, M.; Mereiter, K.; Schmid, R.; Kirchner, K. Chem. Eur. J. 1998, 4, 2043. (j) Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158 (k) Huang, D.; Oliván, M.; Huffman, J. C.; Eisenstein, O.; Caulton, K G. Organometallics 1998, 17, 4700.
16. For recent references see: (a) Albertin, G.; Antoniutti, S.; Bordignon, E.; Cazzaro, F.; Ianelli, S.; Pellizi, G. Organometallics 1995, 14, 4114. (b) Wang, Y.; Finn, M. G. J. Am. Chem. Soc. 1995, 117, 8045. (c) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (d) Braun, T.; Meuer, P.; Werner, H. Organometallics 1996, 15, 4075. (e) Ting, P. C.; Lin, Y. C.; Lee, G. H.; Cheng, M. C.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 6433. (f) Yang, S. M.; Chan, M. C. W.; Cheung, K. K.; Che, C. M.; Peng, S. M. Organometallics 1997, 16, 2819. (g) Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Am. Chem. Soc. 1998, 120, 6175. (h) Jia, G.; Lau, C. P. J. Organomet. Chem. 1998, 565, 37, and references therein. (i) Slugovc, C.; Mauthner, K.; Kacetl, M.; Mereiter, K.; Schmid, R.; Kirchner, K. Chem. Eur. J. 1998, 4, 2043. (j) Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158 (k) Huang, D.; Oliván, M.; Huffman, J. C.; Eisenstein, O.; Caulton, K G. Organometallics 1998, 17, 4700.
17. For recent references see: (a) Albertin, G.; Antoniutti, S.; Bordignon, E.; Cazzaro, F.; Ianelli, S.; Pellizi, G. Organometallics 1995, 14, 4114. (b) Wang, Y.; Finn, M. G. J. Am. Chem. Soc. 1995, 117, 8045. (c) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (d) Braun, T.; Meuer, P.; Werner, H. Organometallics 1996, 15, 4075. (e) Ting, P. C.; Lin, Y. C.; Lee, G. H.; Cheng, M. C.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 6433. (f) Yang, S. M.; Chan, M. C. W.; Cheung, K. K.; Che, C. M.; Peng, S. M. Organometallics 1997, 16, 2819. (g) Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Am. Chem. Soc. 1998, 120, 6175. (h) Jia, G.; Lau, C. P. J. Organomet. Chem. 1998, 565, 37, and references therein. (i) Slugovc, C.; Mauthner, K.; Kacetl, M.; Mereiter, K.; Schmid, R.; Kirchner, K. Chem. Eur. J. 1998, 4, 2043. (j) Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158 (k) Huang, D.; Oliván, M.; Huffman, J. C.; Eisenstein, O.; Caulton, K G. Organometallics 1998, 17, 4700.
18. For recent references see: (a) Albertin, G.; Antoniutti, S.; Bordignon, E.; Cazzaro, F.; Ianelli, S.; Pellizi, G. Organometallics 1995, 14, 4114. (b) Wang, Y.; Finn, M. G. J. Am. Chem. Soc. 1995, 117, 8045. (c) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (d) Braun, T.; Meuer, P.; Werner, H. Organometallics 1996, 15, 4075. (e) Ting, P. C.; Lin, Y. C.; Lee, G. H.; Cheng, M. C.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 6433. (f) Yang, S. M.; Chan, M. C. W.; Cheung, K. K.; Che, C. M.; Peng, S. M. Organometallics 1997, 16, 2819. (g) Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Am. Chem. Soc. 1998, 120, 6175. (h) Jia, G.; Lau, C. P. J. Organomet. Chem. 1998, 565, 37, and references therein. (i) Slugovc, C.; Mauthner, K.; Kacetl, M.; Mereiter, K.; Schmid, R.; Kirchner, K. Chem. Eur. J. 1998, 4, 2043. (j) Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158 (k) Huang, D.; Oliván, M.; Huffman, J. C.; Eisenstein, O.; Caulton, K G. Organometallics 1998, 17, 4700.
19. For recent references see: (a) Albertin, G.; Antoniutti, S.; Bordignon, E.; Cazzaro, F.; Ianelli, S.; Pellizi, G. Organometallics 1995, 14, 4114. (b) Wang, Y.; Finn, M. G. J. Am. Chem. Soc. 1995, 117, 8045. (c) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (d) Braun, T.; Meuer, P.; Werner, H. Organometallics 1996, 15, 4075. (e) Ting, P. C.; Lin, Y. C.; Lee, G. H.; Cheng, M. C.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 6433. (f) Yang, S. M.; Chan, M. C. W.; Cheung, K. K.; Che, C. M.; Peng, S. M. Organometallics 1997, 16, 2819. (g) Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Am. Chem. Soc. 1998, 120, 6175. (h) Jia, G.; Lau, C. P. J. Organomet. Chem. 1998, 565, 37, and references therein. (i) Slugovc, C.; Mauthner, K.; Kacetl, M.; Mereiter, K.; Schmid, R.; Kirchner, K. Chem. Eur. J. 1998, 4, 2043. (j) Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158 (k) Huang, D.; Oliván, M.; Huffman, J. C.; Eisenstein, O.; Caulton, K G. Organometallics 1998, 17, 4700.
20. For recent references see: (a) Albertin, G.; Antoniutti, S.; Bordignon, E.; Cazzaro, F.; Ianelli, S.; Pellizi, G. Organometallics 1995, 14, 4114. (b) Wang, Y.; Finn, M. G. J. Am. Chem. Soc. 1995, 117, 8045. (c) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (d) Braun, T.; Meuer, P.; Werner, H. Organometallics 1996, 15, 4075. (e) Ting, P. C.; Lin, Y. C.; Lee, G. H.; Cheng, M. C.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 6433. (f) Yang, S. M.; Chan, M. C. W.; Cheung, K. K.; Che, C. M.; Peng, S. M. Organometallics 1997, 16, 2819. (g) Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Am. Chem. Soc. 1998, 120, 6175. (h) Jia, G.; Lau, C. P. J. Organomet. Chem. 1998, 565, 37, and references therein. (i) Slugovc, C.; Mauthner, K.; Kacetl, M.; Mereiter, K.; Schmid, R.; Kirchner, K. Chem. Eur. J. 1998, 4, 2043. (j) Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158 (k) Huang, D.; Oliván, M.; Huffman, J. C.; Eisenstein, O.; Caulton, K G. Organometallics 1998, 17, 4700.
21. For recent references see: (a) Albertin, G.; Antoniutti, S.; Bordignon, E.; Cazzaro, F.; Ianelli, S.; Pellizi, G. Organometallics 1995, 14, 4114. (b) Wang, Y.; Finn, M. G. J. Am. Chem. Soc. 1995, 117, 8045. (c) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (d) Braun, T.; Meuer, P.; Werner, H. Organometallics 1996, 15, 4075. (e) Ting, P. C.; Lin, Y. C.; Lee, G. H.; Cheng, M. C.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 6433. (f) Yang, S. M.; Chan, M. C. W.; Cheung, K. K.; Che, C. M.; Peng, S. M. Organometallics 1997, 16, 2819. (g) Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Am. Chem. Soc. 1998, 120, 6175. (h) Jia, G.; Lau, C. P. J. Organomet. Chem. 1998, 565, 37, and references therein. (i) Slugovc, C.; Mauthner, K.; Kacetl, M.; Mereiter, K.; Schmid, R.; Kirchner, K. Chem. Eur. J. 1998, 4, 2043. (j) Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158 (k) Huang, D.; Oliván, M.; Huffman, J. C.; Eisenstein, O.; Caulton, K G. Organometallics 1998, 17, 4700.
22. For recent references see: (a) Albertin, G.; Antoniutti, S.; Bordignon, E.; Cazzaro, F.; Ianelli, S.; Pellizi, G. Organometallics 1995, 14, 4114. (b) Wang, Y.; Finn, M. G. J. Am. Chem. Soc. 1995, 117, 8045. (c) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (d) Braun, T.; Meuer, P.; Werner, H. Organometallics 1996, 15, 4075. (e) Ting, P. C.; Lin, Y. C.; Lee, G. H.; Cheng, M. C.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 6433. (f) Yang, S. M.; Chan, M. C. W.; Cheung, K. K.; Che, C. M.; Peng, S. M. Organometallics 1997, 16, 2819. (g) Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Am. Chem. Soc. 1998, 120, 6175. (h) Jia, G.; Lau, C. P. J. Organomet. Chem. 1998, 565, 37, and references therein. (i) Slugovc, C.; Mauthner, K.; Kacetl, M.; Mereiter, K.; Schmid, R.; Kirchner, K. Chem. Eur. J. 1998, 4, 2043. (j) Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158 (k) Huang, D.; Oliván, M.; Huffman, J. C.; Eisenstein, O.; Caulton, K G. Organometallics 1998, 17, 4700.
23. For recent references see: (a) Wakatsuki, Y.; Yamazaki, H. J. Organomet. Chem. 1995, 500, 349, and references therein. (b) Trost, B. M. Chem. Ber. 1996, 129, 1313, and references therein. (c) Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319. (d) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968. (e) Gemel, C.; Trimmel, G.; Slugovc, C.; Kremel, S.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 3998. (f) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275. (g) Gemel, C.; Kickelbick, G.; Schmid, R.; Kirchner, K. J. Chem. Soc., Dalton Trans. 1997, 2113. (h) Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507, and references therein. (i) Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. Engl. 1998, 77, 2867. (j) Trost, B. M.; Vidal, B.; Thommen, M. Chem. Eur. J. 1999, 5, 1055.
24. For recent references see: (a) Wakatsuki, Y.; Yamazaki, H. J. Organomet. Chem. 1995, 500, 349, and references therein. (b) Trost, B. M. Chem. Ber. 1996, 129, 1313, and references therein. (c) Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319. (d) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968. (e) Gemel, C.; Trimmel, G.; Slugovc, C.; Kremel, S.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 3998. (f) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275. (g) Gemel, C.; Kickelbick, G.; Schmid, R.; Kirchner, K. J. Chem. Soc., Dalton Trans. 1997, 2113. (h) Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507, and references therein. (i) Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. Engl. 1998, 77, 2867. (j) Trost, B. M.; Vidal, B.; Thommen, M. Chem. Eur. J. 1999, 5, 1055.
25. For recent references see: (a) Wakatsuki, Y.; Yamazaki, H. J. Organomet. Chem. 1995, 500, 349, and references therein. (b) Trost, B. M. Chem. Ber. 1996, 129, 1313, and references therein. (c) Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319. (d) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968. (e) Gemel, C.; Trimmel, G.; Slugovc, C.; Kremel, S.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 3998. (f) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275. (g) Gemel, C.; Kickelbick, G.; Schmid, R.; Kirchner, K. J. Chem. Soc., Dalton Trans. 1997, 2113. (h) Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507, and references therein. (i) Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. Engl. 1998, 77, 2867. (j) Trost, B. M.; Vidal, B.; Thommen, M. Chem. Eur. J. 1999, 5, 1055.
26. For recent references see: (a) Wakatsuki, Y.; Yamazaki, H. J. Organomet. Chem. 1995, 500, 349, and references therein. (b) Trost, B. M. Chem. Ber. 1996, 129, 1313, and references therein. (c) Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319. (d) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968. (e) Gemel, C.; Trimmel, G.; Slugovc, C.; Kremel, S.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 3998. (f) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275. (g) Gemel, C.; Kickelbick, G.; Schmid, R.; Kirchner, K. J. Chem. Soc., Dalton Trans. 1997, 2113. (h) Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507, and references therein. (i) Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. Engl. 1998, 77, 2867. (j) Trost, B. M.; Vidal, B.; Thommen, M. Chem. Eur. J. 1999, 5, 1055.
27. For recent references see: (a) Wakatsuki, Y.; Yamazaki, H. J. Organomet. Chem. 1995, 500, 349, and references therein. (b) Trost, B. M. Chem. Ber. 1996, 129, 1313, and references therein. (c) Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319. (d) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968. (e) Gemel, C.; Trimmel, G.; Slugovc, C.; Kremel, S.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 3998. (f) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275. (g) Gemel, C.; Kickelbick, G.; Schmid, R.; Kirchner, K. J. Chem. Soc., Dalton Trans. 1997, 2113. (h) Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507, and references therein. (i) Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. Engl. 1998, 77, 2867. (j) Trost, B. M.; Vidal, B.; Thommen, M. Chem. Eur. J. 1999, 5, 1055.
28. For recent references see: (a) Wakatsuki, Y.; Yamazaki, H. J. Organomet. Chem. 1995, 500, 349, and references therein. (b) Trost, B. M. Chem. Ber. 1996, 129, 1313, and references therein. (c) Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319. (d) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968. (e) Gemel, C.; Trimmel, G.; Slugovc, C.; Kremel, S.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 3998. (f) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275. (g) Gemel, C.; Kickelbick, G.; Schmid, R.; Kirchner, K. J. Chem. Soc., Dalton Trans. 1997, 2113. (h) Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507, and references therein. (i) Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. Engl. 1998, 77, 2867. (j) Trost, B. M.; Vidal, B.; Thommen, M. Chem. Eur. J. 1999, 5, 1055.
29. For recent references see: (a) Wakatsuki, Y.; Yamazaki, H. J. Organomet. Chem. 1995, 500, 349, and references therein. (b) Trost, B. M. Chem. Ber. 1996, 129, 1313, and references therein. (c) Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319. (d) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968. (e) Gemel, C.; Trimmel, G.; Slugovc, C.; Kremel, S.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 3998. (f) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275. (g) Gemel, C.; Kickelbick, G.; Schmid, R.; Kirchner, K. J. Chem. Soc., Dalton Trans. 1997, 2113. (h) Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507, and references therein. (i) Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. Engl. 1998, 77, 2867. (j) Trost, B. M.; Vidal, B.; Thommen, M. Chem. Eur. J. 1999, 5, 1055.
30. For recent references see: (a) Wakatsuki, Y.; Yamazaki, H. J. Organomet. Chem. 1995, 500, 349, and references therein. (b) Trost, B. M. Chem. Ber. 1996, 129, 1313, and references therein. (c) Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319. (d) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968. (e) Gemel, C.; Trimmel, G.; Slugovc, C.; Kremel, S.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 3998. (f) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275. (g) Gemel, C.; Kickelbick, G.; Schmid, R.; Kirchner, K. J. Chem. Soc., Dalton Trans. 1997, 2113. (h) Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507, and references therein. (i) Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. Engl. 1998, 77, 2867. (j) Trost, B. M.; Vidal, B.; Thommen, M. Chem. Eur. J. 1999, 5, 1055.
31. For recent references see: (a) Wakatsuki, Y.; Yamazaki, H. J. Organomet. Chem. 1995, 500, 349, and references therein. (b) Trost, B. M. Chem. Ber. 1996, 129, 1313, and references therein. (c) Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319. (d) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968. (e) Gemel, C.; Trimmel, G.; Slugovc, C.; Kremel, S.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 3998. (f) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275. (g) Gemel, C.; Kickelbick, G.; Schmid, R.; Kirchner, K. J. Chem. Soc., Dalton Trans. 1997, 2113. (h) Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507, and references therein. (i) Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. Engl. 1998, 77, 2867. (j) Trost, B. M.; Vidal, B.; Thommen, M. Chem. Eur. J. 1999, 5, 1055.
32. For recent references see: (a) Wakatsuki, Y.; Yamazaki, H. J. Organomet. Chem. 1995, 500, 349, and references therein. (b) Trost, B. M. Chem. Ber. 1996, 129, 1313, and references therein. (c) Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319. (d) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968. (e) Gemel, C.; Trimmel, G.; Slugovc, C.; Kremel, S.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 3998. (f) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275. (g) Gemel, C.; Kickelbick, G.; Schmid, R.; Kirchner, K. J. Chem. Soc., Dalton Trans. 1997, 2113. (h) Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507, and references therein. (i) Tokunaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. Engl. 1998, 77, 2867. (j) Trost, B. M.; Vidal, B.; Thommen, M. Chem. Eur. J. 1999, 5, 1055.
33. + (dippe = 1,2-bis(diisopropylphosphino)ethane) have been recently found to be involved in the formation of the corresponding vinylidene complexes, de los Rios, I.; Jiménez Tenorio, M.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 1997, 119, 6529.
34. (a) Silvestre, J.; Hoffmann, R. Helv. Chim. Acta 1985, 68, 1461.
35. (b) Wakatsuki, Y.; Koga, N.; Yamazaki, H.; Morokuma, K. J. Am. Chem. Soc. 1994, 116, 8105.
36. (c) Wakatsuki, Y.; Koga, N.; Werner, H.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 360.
37. (d) Stegmann, R.; Frenking, G. Organometallics 1998, 17, 2089.
38. (a) Bullock, R. M. J. Chem. Soc., Chem. Commun. 1989, 165.
39. (b) Lomprey, J. R.; Selegue, J. P. J. Am. Chem. Soc. 1992, 114, 5518.
40. Gamasa, M. P.; Gimeno, J.; González-Bernardo, C.; Borge, J.; Garcia-Granda, S. Organometallics 1997, 16, 2483.
41. (a) Martín, M.; Gevert, O.; Werner, H. J. Chem. Soc., Dalton Trans. 1996, 2275.
42. (b) Bianchini, C.; Purches, G.; Zanobini, F.; Peruzzini, M. Inorg. Chim. Acta 1998, 272, 1.
43. 2-alkyne isomerizations have been also reported: (a) Ru: Slugovc, C.; Sapunov, V. N.; Wiede, P.; Mereiter, K.; Schinid, R.; Kirchner, K. J. Chem. Soc., Dalton Trans. 1997, 4209. (b) Fe: Bly, R. S.; Zhong, Z.; Kane, C.; Bly, R. K. Organometallics 1994, 13, 899, and references therein. (c) Mo, W: Ipaktschi, J.; Demuth-Eberle, G. J.; Mirzaei, F.; Muller, B. G.; Beck, J.; Serafin, M. Organometallics 1995, 14, 3335.
44. 2-alkyne isomerizations have been also reported: (a) Ru: Slugovc, C.; Sapunov, V. N.; Wiede, P.; Mereiter, K.; Schinid, R.; Kirchner, K. J. Chem. Soc., Dalton Trans. 1997, 4209. (b) Fe: Bly, R. S.; Zhong, Z.; Kane, C.; Bly, R. K. Organometallics 1994, 13, 899, and references therein. (c) Mo, W: Ipaktschi, J.; Demuth-Eberle, G. J.; Mirzaei, F.; Muller, B. G.; Beck, J.; Serafin, M. Organometallics 1995, 14, 3335.
45. 2-alkyne isomerizations have been also reported: (a) Ru: Slugovc, C.; Sapunov, V. N.; Wiede, P.; Mereiter, K.; Schinid, R.; Kirchner, K. J. Chem. Soc., Dalton Trans. 1997, 4209. (b) Fe: Bly, R. S.; Zhong, Z.; Kane, C.; Bly, R. K. Organometallics 1994, 13, 899, and references therein. (c) Mo, W: Ipaktschi, J.; Demuth-Eberle, G. J.; Mirzaei, F.; Muller, B. G.; Beck, J.; Serafin, M. Organometallics 1995, 14, 3335.
46. (a) Gamasa, M. P.; Gimeno, J.; Martín-Vaca, B. M.; Borge, J.; García-Granda, S.; Pérez-Carreño, E. Organometallics 1994, 13, 4045.
47. (b) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Borge, J.; García-Granda, S. J. Chem. Soc., Chem. Commun. 1994, 2495.
48. (c) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; González-Cueva, M.; Lastra, E.; Borge, J.; García-Granda, S. Organometallics 1996, 15, 2137.
49. (d) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Borge, J.; García-Granda, S. Organometallics 1997, 16, 3178.
50. (e) Cadierno, V., Gamasa, M. P.; Gimeno, J.; López-González, M. C.; Borge, J.; García-Granda, S. Organometallics 1997, 16, 4453.
51. (f) Crochet, P.; Demerseman, B.; Vallejo, M. I.; Gamasa, M. P.; Gimeno, J.; Borge, J.; García-Granda, S. Organometallics 1997, 16, 5406.
52. (g) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Moretó, J. M.; Ricart, S.; Roig, A.; Molins, E. Organometallics 1998, 17, 697.
53. (h) Gamasa, M. P.; Gimeno, J.; Martín-Vaca, B. M. Organometallics 1998, 17, 3707.
54. (i) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Pérez-Carreño, E.; Ienco, A. Organometallics 1998, 17, 5216.
55. (j) Perez-Carreño, E. Doctoral Thesis, University of Oviedo, 1996.
56. 6] (Unpublished results).
57. 2 solutions of the vinylidene complex 1. No products other than 1 could be detected.
58. (a) Houbrechts, S.; Clays, K.; Persoons, A.; Cadierno, V.; Gamasa, M. P.; Gimeno, J. Organometallics 1996, 15, 5266.
59. (b) Cadierno, V.; Conejero, S.; Gamasa, M. P.; Gimeno, J.; Asselberghs, I.; Houbrechts, S.; Clays, K.; Persoons, A.; Borge, J.; García-Granda, S. Organometallics 1999, 18, 582.
60. Enynes 8a,b have been previously reported. 8a: (a) Jasiobedzki, W.; Zimniak, A.; Glinka, T. Rocz. Chem. 1975, 49, 111. 8b: (b) Gibson, A. W.; Humphrey, G. R.; Kennedy, D. J.; Wright, S. H. B. Synthesis 1991, 414.
61. Enynes 8a,b have been previously reported. 8a: (a) Jasiobedzki, W.; Zimniak, A.; Glinka, T. Rocz. Chem. 1975, 49, 111. 8b: (b) Gibson, A. W.; Humphrey, G. R.; Kennedy, D. J.; Wright, S. H. B. Synthesis 1991, 414.
62. See for example: (a) Pattenden, G. In Comprehensive Organic Chemistry, Vol 1; Stoddart, J. F., Ed.; Pergamon: Oxford, 1979; p 205. (b) Yamamoto, H. In Comprehensive Organic Synthesis, Vol 2; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 91. (c) Cheshire, D. R. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 217. (d) Sonogashira, K. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 521. (e) Coveney, D. J. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 878.
63. See for example: (a) Pattenden, G. In Comprehensive Organic Chemistry, Vol 1; Stoddart, J. F., Ed.; Pergamon: Oxford, 1979; p 205. (b) Yamamoto, H. In Comprehensive Organic Synthesis, Vol 2; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 91. (c) Cheshire, D. R. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 217. (d) Sonogashira, K. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 521. (e) Coveney, D. J. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 878.
64. See for example: (a) Pattenden, G. In Comprehensive Organic Chemistry, Vol 1; Stoddart, J. F., Ed.; Pergamon: Oxford, 1979; p 205. (b) Yamamoto, H. In Comprehensive Organic Synthesis, Vol 2; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 91. (c) Cheshire, D. R. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 217. (d) Sonogashira, K. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 521. (e) Coveney, D. J. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 878.
65. See for example: (a) Pattenden, G. In Comprehensive Organic Chemistry, Vol 1; Stoddart, J. F., Ed.; Pergamon: Oxford, 1979; p 205. (b) Yamamoto, H. In Comprehensive Organic Synthesis, Vol 2; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 91. (c) Cheshire, D. R. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 217. (d) Sonogashira, K. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 521. (e) Coveney, D. J. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 878.
66. See for example: (a) Pattenden, G. In Comprehensive Organic Chemistry, Vol 1; Stoddart, J. F., Ed.; Pergamon: Oxford, 1979; p 205. (b) Yamamoto, H. In Comprehensive Organic Synthesis, Vol 2; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 91. (c) Cheshire, D. R. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 217. (d) Sonogashira, K. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 521. (e) Coveney, D. J. In Comprehensive Organic Synthesis, Vol 3; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; p 878.
67. n as base has been reported to yield trimethylsilyl-protected (E)-1,3-enynes in good yields. Corey, E. J.; Ruden, R. A. Tetrahedron Lett. 1973, 1495.
68. n as base has been reported to yield trimethylsilyl-protected (E)-1,3-enynes in good yields. Corey, E. J.; Ruden, R. A. Tetrahedron Lett. 1973, 1495.
69. 6]-stabilized propargylium ions, is known to yield γ-keto-substituted alkynes. (a) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207. (b) Smit, W. A.; Caple, R.; Smoliakova, I. P. Chem. Rev. 1994, 94, 2359.
70. 6]-stabilized propargylium ions, is known to yield γ-keto-substituted alkynes. (a) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207. (b) Smit, W. A.; Caple, R.; Smoliakova, I. P. Chem. Rev. 1994, 94, 2359.
71. Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Lastra, E.; Borge, J.; Garda-Granda, S. Organometallics 1994, 13, 745.
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73. [Co]: (a) Bianchini, C.; Peruzzini, M.; Vacca A.; Zanobini, F. Organometallics 1991, 10, 3697. [Rh]: (b) Wolf, J.; Werner, H.; Sehadli, O.; Ziegler, M. L. Angew, Chem., Int. Ed. Engl. 1983, 22, 414. (c) Werner, H.; Garcia Alonso, F. J.; Otto, H.; Wolf, J. Z. Naturforsch 1988, 43b, 722. (d) Werner, H.; Brekau, U. Z. Naturforsch. 1989, 44b, 1438. (e) Rappert, T.; Nurnberg, O.; Mahr, N.; Wolf, J.; Werner, H. Organometallics 1992, 11, 4156. (f) Werner, H.; Baum, M.; Schneider, D.; Windmuller, B. Organometallics 1994, 13, 1089. (g) Werner, H.; Rappert, T.; Baum, M.; Stark, A. J. Organomet. Chem. 1993, 459, 319. [Ir]: (h) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 406. (i) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. J. Chem. Soc., Chem. Commun. 1987, 852. (j) Hoehn, A.; Werner, H. J. Organomet. Chem. 1990, 382, 255. (k) Werner, H.; Hoehn, A.; Schulz, M. J. Chem. Soc., Dalton Trans. 1991, 777.
74. [Co]: (a) Bianchini, C.; Peruzzini, M.; Vacca A.; Zanobini, F. Organometallics 1991, 10, 3697. [Rh]: (b) Wolf, J.; Werner, H.; Sehadli, O.; Ziegler, M. L. Angew, Chem., Int. Ed. Engl. 1983, 22, 414. (c) Werner, H.; Garcia Alonso, F. J.; Otto, H.; Wolf, J. Z. Naturforsch 1988, 43b, 722. (d) Werner, H.; Brekau, U. Z. Naturforsch. 1989, 44b, 1438. (e) Rappert, T.; Nurnberg, O.; Mahr, N.; Wolf, J.; Werner, H. Organometallics 1992, 11, 4156. (f) Werner, H.; Baum, M.; Schneider, D.; Windmuller, B. Organometallics 1994, 13, 1089. (g) Werner, H.; Rappert, T.; Baum, M.; Stark, A. J. Organomet. Chem. 1993, 459, 319. [Ir]: (h) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 406. (i) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. J. Chem. Soc., Chem. Commun. 1987, 852. (j) Hoehn, A.; Werner, H. J. Organomet. Chem. 1990, 382, 255. (k) Werner, H.; Hoehn, A.; Schulz, M. J. Chem. Soc., Dalton Trans. 1991, 777.
75. [Co]: (a) Bianchini, C.; Peruzzini, M.; Vacca A.; Zanobini, F. Organometallics 1991, 10, 3697. [Rh]: (b) Wolf, J.; Werner, H.; Sehadli, O.; Ziegler, M. L. Angew, Chem., Int. Ed. Engl. 1983, 22, 414. (c) Werner, H.; Garcia Alonso, F. J.; Otto, H.; Wolf, J. Z. Naturforsch 1988, 43b, 722. (d) Werner, H.; Brekau, U. Z. Naturforsch. 1989, 44b, 1438. (e) Rappert, T.; Nurnberg, O.; Mahr, N.; Wolf, J.; Werner, H. Organometallics 1992, 11, 4156. (f) Werner, H.; Baum, M.; Schneider, D.; Windmuller, B. Organometallics 1994, 13, 1089. (g) Werner, H.; Rappert, T.; Baum, M.; Stark, A. J. Organomet. Chem. 1993, 459, 319. [Ir]: (h) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 406. (i) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. J. Chem. Soc., Chem. Commun. 1987, 852. (j) Hoehn, A.; Werner, H. J. Organomet. Chem. 1990, 382, 255. (k) Werner, H.; Hoehn, A.; Schulz, M. J. Chem. Soc., Dalton Trans. 1991, 777.
76. [Co]: (a) Bianchini, C.; Peruzzini, M.; Vacca A.; Zanobini, F. Organometallics 1991, 10, 3697. [Rh]: (b) Wolf, J.; Werner, H.; Sehadli, O.; Ziegler, M. L. Angew, Chem., Int. Ed. Engl. 1983, 22, 414. (c) Werner, H.; Garcia Alonso, F. J.; Otto, H.; Wolf, J. Z. Naturforsch 1988, 43b, 722. (d) Werner, H.; Brekau, U. Z. Naturforsch. 1989, 44b, 1438. (e) Rappert, T.; Nurnberg, O.; Mahr, N.; Wolf, J.; Werner, H. Organometallics 1992, 11, 4156. (f) Werner, H.; Baum, M.; Schneider, D.; Windmuller, B. Organometallics 1994, 13, 1089. (g) Werner, H.; Rappert, T.; Baum, M.; Stark, A. J. Organomet. Chem. 1993, 459, 319. [Ir]: (h) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 406. (i) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. J. Chem. Soc., Chem. Commun. 1987, 852. (j) Hoehn, A.; Werner, H. J. Organomet. Chem. 1990, 382, 255. (k) Werner, H.; Hoehn, A.; Schulz, M. J. Chem. Soc., Dalton Trans. 1991, 777.
77. [Co]: (a) Bianchini, C.; Peruzzini, M.; Vacca A.; Zanobini, F. Organometallics 1991, 10, 3697. [Rh]: (b) Wolf, J.; Werner, H.; Sehadli, O.; Ziegler, M. L. Angew, Chem., Int. Ed. Engl. 1983, 22, 414. (c) Werner, H.; Garcia Alonso, F. J.; Otto, H.; Wolf, J. Z. Naturforsch 1988, 43b, 722. (d) Werner, H.; Brekau, U. Z. Naturforsch. 1989, 44b, 1438. (e) Rappert, T.; Nurnberg, O.; Mahr, N.; Wolf, J.; Werner, H. Organometallics 1992, 11, 4156. (f) Werner, H.; Baum, M.; Schneider, D.; Windmuller, B. Organometallics 1994, 13, 1089. (g) Werner, H.; Rappert, T.; Baum, M.; Stark, A. J. Organomet. Chem. 1993, 459, 319. [Ir]: (h) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 406. (i) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. J. Chem. Soc., Chem. Commun. 1987, 852. (j) Hoehn, A.; Werner, H. J. Organomet. Chem. 1990, 382, 255. (k) Werner, H.; Hoehn, A.; Schulz, M. J. Chem. Soc., Dalton Trans. 1991, 777.
78. [Co]: (a) Bianchini, C.; Peruzzini, M.; Vacca A.; Zanobini, F. Organometallics 1991, 10, 3697. [Rh]: (b) Wolf, J.; Werner, H.; Sehadli, O.; Ziegler, M. L. Angew, Chem., Int. Ed. Engl. 1983, 22, 414. (c) Werner, H.; Garcia Alonso, F. J.; Otto, H.; Wolf, J. Z. Naturforsch 1988, 43b, 722. (d) Werner, H.; Brekau, U. Z. Naturforsch. 1989, 44b, 1438. (e) Rappert, T.; Nurnberg, O.; Mahr, N.; Wolf, J.; Werner, H. Organometallics 1992, 11, 4156. (f) Werner, H.; Baum, M.; Schneider, D.; Windmuller, B. Organometallics 1994, 13, 1089. (g) Werner, H.; Rappert, T.; Baum, M.; Stark, A. J. Organomet. Chem. 1993, 459, 319. [Ir]: (h) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 406. (i) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. J. Chem. Soc., Chem. Commun. 1987, 852. (j) Hoehn, A.; Werner, H. J. Organomet. Chem. 1990, 382, 255. (k) Werner, H.; Hoehn, A.; Schulz, M. J. Chem. Soc., Dalton Trans. 1991, 777.
79. [Co]: (a) Bianchini, C.; Peruzzini, M.; Vacca A.; Zanobini, F. Organometallics 1991, 10, 3697. [Rh]: (b) Wolf, J.; Werner, H.; Sehadli, O.; Ziegler, M. L. Angew, Chem., Int. Ed. Engl. 1983, 22, 414. (c) Werner, H.; Garcia Alonso, F. J.; Otto, H.; Wolf, J. Z. Naturforsch 1988, 43b, 722. (d) Werner, H.; Brekau, U. Z. Naturforsch. 1989, 44b, 1438. (e) Rappert, T.; Nurnberg, O.; Mahr, N.; Wolf, J.; Werner, H. Organometallics 1992, 11, 4156. (f) Werner, H.; Baum, M.; Schneider, D.; Windmuller, B. Organometallics 1994, 13, 1089. (g) Werner, H.; Rappert, T.; Baum, M.; Stark, A. J. Organomet. Chem. 1993, 459, 319. [Ir]: (h) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 406. (i) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. J. Chem. Soc., Chem. Commun. 1987, 852. (j) Hoehn, A.; Werner, H. J. Organomet. Chem. 1990, 382, 255. (k) Werner, H.; Hoehn, A.; Schulz, M. J. Chem. Soc., Dalton Trans. 1991, 777.
80. [Co]: (a) Bianchini, C.; Peruzzini, M.; Vacca A.; Zanobini, F. Organometallics 1991, 10, 3697. [Rh]: (b) Wolf, J.; Werner, H.; Sehadli, O.; Ziegler, M. L. Angew, Chem., Int. Ed. Engl. 1983, 22, 414. (c) Werner, H.; Garcia Alonso, F. J.; Otto, H.; Wolf, J. Z. Naturforsch 1988, 43b, 722. (d) Werner, H.; Brekau, U. Z. Naturforsch. 1989, 44b, 1438. (e) Rappert, T.; Nurnberg, O.; Mahr, N.; Wolf, J.; Werner, H. Organometallics 1992, 11, 4156. (f) Werner, H.; Baum, M.; Schneider, D.; Windmuller, B. Organometallics 1994, 13, 1089. (g) Werner, H.; Rappert, T.; Baum, M.; Stark, A. J. Organomet. Chem. 1993, 459, 319. [Ir]: (h) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 406. (i) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. J. Chem. Soc., Chem. Commun. 1987, 852. (j) Hoehn, A.; Werner, H. J. Organomet. Chem. 1990, 382, 255. (k) Werner, H.; Hoehn, A.; Schulz, M. J. Chem. Soc., Dalton Trans. 1991, 777.
81. [Co]: (a) Bianchini, C.; Peruzzini, M.; Vacca A.; Zanobini, F. Organometallics 1991, 10, 3697. [Rh]: (b) Wolf, J.; Werner, H.; Sehadli, O.; Ziegler, M. L. Angew, Chem., Int. Ed. Engl. 1983, 22, 414. (c) Werner, H.; Garcia Alonso, F. J.; Otto, H.; Wolf, J. Z. Naturforsch 1988, 43b, 722. (d) Werner, H.; Brekau, U. Z. Naturforsch. 1989, 44b, 1438. (e) Rappert, T.; Nurnberg, O.; Mahr, N.; Wolf, J.; Werner, H. Organometallics 1992, 11, 4156. (f) Werner, H.; Baum, M.; Schneider, D.; Windmuller, B. Organometallics 1994, 13, 1089. (g) Werner, H.; Rappert, T.; Baum, M.; Stark, A. J. Organomet. Chem. 1993, 459, 319. [Ir]: (h) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 406. (i) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. J. Chem. Soc., Chem. Commun. 1987, 852. (j) Hoehn, A.; Werner, H. J. Organomet. Chem. 1990, 382, 255. (k) Werner, H.; Hoehn, A.; Schulz, M. J. Chem. Soc., Dalton Trans. 1991, 777.
82. [Co]: (a) Bianchini, C.; Peruzzini, M.; Vacca A.; Zanobini, F. Organometallics 1991, 10, 3697. [Rh]: (b) Wolf, J.; Werner, H.; Sehadli, O.; Ziegler, M. L. Angew, Chem., Int. Ed. Engl. 1983, 22, 414. (c) Werner, H.; Garcia Alonso, F. J.; Otto, H.; Wolf, J. Z. Naturforsch 1988, 43b, 722. (d) Werner, H.; Brekau, U. Z. Naturforsch. 1989, 44b, 1438. (e) Rappert, T.; Nurnberg, O.; Mahr, N.; Wolf, J.; Werner, H. Organometallics 1992, 11, 4156. (f) Werner, H.; Baum, M.; Schneider, D.; Windmuller, B. Organometallics 1994, 13, 1089. (g) Werner, H.; Rappert, T.; Baum, M.; Stark, A. J. Organomet. Chem. 1993, 459, 319. [Ir]: (h) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. Angew. Chem., Int. Ed. Engl. 1985, 24, 406. (i) Hoehn, A.; Otto, H.; Dziallas, M.; Werner, H. J. Chem. Soc., Chem. Commun. 1987, 852. (j) Hoehn, A.; Werner, H. J. Organomet. Chem. 1990, 382, 255. (k) Werner, H.; Hoehn, A.; Schulz, M. J. Chem. Soc., Dalton Trans. 1991, 777.
83. + (dippe = l,2-bis(diisopropylphosphino)ethane) C. Puerta and co-workers have also isolated a metastable hydrido-alkynyl intermediate (see ref 5). However, since this reaction is inhibited in solution by strong acids, the mechanism seems to be dissociative in contrast to the usual 1,3-[H] shift, indicating that the isomerization proceeds in a nonconcerted fashion.
84. We have explored the alternative mechanism (path B; Chart 1) with a single calculation of the optimized structure energy of the corresponding hydrido-alkynyl species, and we have found an energy comparable to the transition state C. This fact allows us to predict that the energy barrier needed for this mechanism should be higher than that of the [1, 2]-H shift process and could explain why this intermediate was not detected.
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