On Early Events in the Pauson - Khand Reaction

Organic Letters

Volumn 5, Issue 22, 2003, Pages 4073-4075

  Gimbert, Yves ^a   Lesage, Denis ^b   Milet, Anne ^a   Fournier, Françoise ^b   Greene, Andrew E ^a   Tabet, Jean Claude ^b  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

^b SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CARBON MONOXIDE;

ARTICLE; CHEMICAL REACTION; MASS SPECTROMETRY; PAUSON KHAND REACTION; TANDEM MASS SPECTROMETRY;

EID: 0344514154     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035503z     Document Type: Article

References (18)

1. (a) Magnus, P.; Exon, C.; Albaugh-Robertson, P. Tetrahedron 1985, 41, 5861-5869.
2. (b) Magnus, P. L.; Principe, M. Tetrahedron Lett. 1985, 26, 4851-4854.
3. For reviews, see: (a) Schore, N. E. Org. React. 1991, 40, 1-90. (b) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297-341. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263-3283. (d) Fletcher, A. J.; Christie, S. D. R. J. Chem. Soc. Perkin Trans. 1 2000, 1657-1668.
4. For reviews, see: (a) Schore, N. E. Org. React. 1991, 40, 1-90. (b) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297-341. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263-3283. (d) Fletcher, A. J.; Christie, S. D. R. J. Chem. Soc. Perkin Trans. 1 2000, 1657-1668.
5. For reviews, see: (a) Schore, N. E. Org. React. 1991, 40, 1-90. (b) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297-341. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263-3283. (d) Fletcher, A. J.; Christie, S. D. R. J. Chem. Soc. Perkin Trans. 1 2000, 1657-1668.
6. For reviews, see: (a) Schore, N. E. Org. React. 1991, 40, 1-90. (b) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297-341. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263-3283. (d) Fletcher, A. J.; Christie, S. D. R. J. Chem. Soc. Perkin Trans. 1 2000, 1657-1668.
7. Complex II (Scheme 1), generated photochemically, has been identified by IR spectroscopy. See: (a) Gordon, G. M.; Kiszka, M.; Dunkin, I. R.; Kerr, W. J. ; Scott, J. S.; Gebicki, J. J. Organomet. Chem. 1988, 554, 147-154. (b) Draper, S. M.; Long, C.; Myers, B. M. J. Organomet. Chem. 1999, 558, 195-199. For ligand stabilization of II, see: (c) Krafft, M. E.; Scott, I. L.; Romero, R. H. ; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207. (d) Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A.; Bernardes, V.; Greene, A. E.; Alvarez-Larena, A.; Piniella, J. F. J. Am. Chem. Soc. 1994, 116, 2153-2154.
8. Complex II (Scheme 1), generated photochemically, has been identified by IR spectroscopy. See: (a) Gordon, G. M.; Kiszka, M.; Dunkin, I. R.; Kerr, W. J. ; Scott, J. S.; Gebicki, J. J. Organomet. Chem. 1988, 554, 147-154. (b) Draper, S. M.; Long, C.; Myers, B. M. J. Organomet. Chem. 1999, 558, 195-199. For ligand stabilization of II, see: (c) Krafft, M. E.; Scott, I. L.; Romero, R. H. ; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207. (d) Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A.; Bernardes, V.; Greene, A. E.; Alvarez-Larena, A.; Piniella, J. F. J. Am. Chem. Soc. 1994, 116, 2153-2154.
9. Complex II (Scheme 1), generated photochemically, has been identified by IR spectroscopy. See: (a) Gordon, G. M.; Kiszka, M.; Dunkin, I. R.; Kerr, W. J. ; Scott, J. S.; Gebicki, J. J. Organomet. Chem. 1988, 554, 147-154. (b) Draper, S. M.; Long, C.; Myers, B. M. J. Organomet. Chem. 1999, 558, 195-199. For ligand stabilization of II, see: (c) Krafft, M. E.; Scott, I. L.; Romero, R. H. ; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207. (d) Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A.; Bernardes, V.; Greene, A. E.; Alvarez-Larena, A.; Piniella, J. F. J. Am. Chem. Soc. 1994, 116, 2153-2154.
10. Complex II (Scheme 1), generated photochemically, has been identified by IR spectroscopy. See: (a) Gordon, G. M.; Kiszka, M.; Dunkin, I. R.; Kerr, W. J. ; Scott, J. S.; Gebicki, J. J. Organomet. Chem. 1988, 554, 147-154. (b) Draper, S. M.; Long, C.; Myers, B. M. J. Organomet. Chem. 1999, 558, 195-199. For ligand stabilization of II, see: (c) Krafft, M. E.; Scott, I. L.; Romero, R. H. ; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199-7207. (d) Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A.; Bernardes, V.; Greene, A. E.; Alvarez-Larena, A.; Piniella, J. F. J. Am. Chem. Soc. 1994, 116, 2153-2154.
11. Dickson, R. S.; Fraser, P. J. Adv. Organomet. Chem. 1974, 12, 323-377.
12. Yamanaka, M.; Nakamura, E. J. Am. Chem. Soc. 2001, 123, 1703-1708.
13. For an excellent review, see: Plattner, D. P. Int. J. Mass Spectrom. 2001, 207, 125-144.
14. Henderson, W.; MacIndoe, J. S.; Nicholson, B. K.; Dyson, P. J. J. Chem. Soc., Dalton Trans. 1998, 519-525.
15. Gimbert, Y.; Robert, F.; Durif, A.; Averbuch, M.-T.; Kann, N.; Greene, A. E. J. Org. Chem. 1999, 64, 3492-3497.
16. -.
17. - was demonstrated by using norbornane in the collision cell, which, as expected, did not produced an adduct ion at m/z 783.
18. For computational details, see: de Bruin, T. J. M.; Milet, A.; Robert, F.; Gimbert, Y.; Greene, A. E. J. Am. Chem. Soc. 2001, 123, 7184-7185.