A novel route to 2-cyclohexenones via reaction of the manganese carbene anions [(η5-MeC5H4)(CO) 2Mn=C(OEt)CHR]- (R = H, Me) with α,β-unsaturated ketones

Organometallics

Volumn 16, Issue 18, 1997, Pages 3873-3875

  Mongin, Carole ^a   Lugan, Noël ^a   Mathieu, René ^a  

^a LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008051959     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9704206     Document Type: Article

References (36)

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13. The detailed experimental, spectroscopic, and crystallographic information are provided as Supporting Information.
14. For a definition of the synlanti convention used, see: Masamune, S.; Ali, Sk. A.; Snitman, D. L.; Garvey, D. S. Angew. Chem., Int. Ed. Engl. 1980, 19, 557.
15. 1H NMR, considering the upfield chemical shift of the substituent gauche to the phenyl ring for the most stable rotamer (hydrogens anti) in each diastereomer, see: Oare, D. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 157.
16. w = 0.0423 for 2171 observations and 244 variable parameters.
17. 3Mn in the presence of 2-cyclohexenone, see: Giffard, M.; Centric, E.; Touchard, D.; Dixneuf, P. J. Organomet. Chem. 1977, 129, 371.
18. w = 0.0443 for 1805 observations and 172 variable parameters.
19. 6
20. w = 0.0623 for 1055 observations and 166 variable parameters.
21. 6
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26. 3 as the only organometallic "byproduct", which may be recycled to regenerate 1.
27. (a) Kugatova-Shemyakina, G. P.; Lutsenko, V. V. Izv. Akad. Nauk SSSR, Ser. Khim. 1962, 8, 1429.
28. (b) For the use of cis/trans-4,5-dimethyl 2-cyclohexenone as a flavoring agent, see: Flament, I. Fr. Pat. Appl. 73.28312, 1973.
29. The synthesis of 5-phenyl-4-methyl 2-cyclohexenone (9h) as a cis/trans mixture has only recently been reported, see: Aurell, M. J.; Gaviña, P.; Mestres, R. Tetrahedron 1994, 50, 2571.
30. For other metal-mediated stoichiometric syntheses of 2-cyclohexeneones, see, for instance: (a) Mortimer, M. D.; Carter, J. D.; McElwee-White, L. Organometallics 1993, 12, 4493. (b) McDaniel, K. F.; Kracker, L. R., II; Thamburaj, P. K. Tetrahedron Lett. 1990, 31, 2373. (c) Potter, G. A.; McCague, R. J. J. Chem. Soc., Chem. Commun 1990, 1172. (d) Muzart, J.; Pale, P.; Pete, J.-P. J. Chem. Soc., Chem. Commun. 1981, 668. (e) Birch, A. J.; Pearson, A. J. J. Chem. Soc., Chem. Commun. 1976, 601.
31. For other metal-mediated stoichiometric syntheses of 2-cyclohexeneones, see, for instance: (a) Mortimer, M. D.; Carter, J. D.; McElwee-White, L. Organometallics 1993, 12, 4493. (b) McDaniel, K. F.; Kracker, L. R., II; Thamburaj, P. K. Tetrahedron Lett. 1990, 31, 2373. (c) Potter, G. A.; McCague, R. J. J. Chem. Soc., Chem. Commun 1990, 1172. (d) Muzart, J.; Pale, P.; Pete, J.-P. J. Chem. Soc., Chem. Commun. 1981, 668. (e) Birch, A. J.; Pearson, A. J. J. Chem. Soc., Chem. Commun. 1976, 601.
32. For other metal-mediated stoichiometric syntheses of 2-cyclohexeneones, see, for instance: (a) Mortimer, M. D.; Carter, J. D.; McElwee-White, L. Organometallics 1993, 12, 4493. (b) McDaniel, K. F.; Kracker, L. R., II; Thamburaj, P. K. Tetrahedron Lett. 1990, 31, 2373. (c) Potter, G. A.; McCague, R. J. J. Chem. Soc., Chem. Commun 1990, 1172. (d) Muzart, J.; Pale, P.; Pete, J.-P. J. Chem. Soc., Chem. Commun. 1981, 668. (e) Birch, A. J.; Pearson, A. J. J. Chem. Soc., Chem. Commun. 1976, 601.
33. For other metal-mediated stoichiometric syntheses of 2-cyclohexeneones, see, for instance: (a) Mortimer, M. D.; Carter, J. D.; McElwee-White, L. Organometallics 1993, 12, 4493. (b) McDaniel, K. F.; Kracker, L. R., II; Thamburaj, P. K. Tetrahedron Lett. 1990, 31, 2373. (c) Potter, G. A.; McCague, R. J. J. Chem. Soc., Chem. Commun 1990, 1172. (d) Muzart, J.; Pale, P.; Pete, J.-P. J. Chem. Soc., Chem. Commun. 1981, 668. (e) Birch, A. J.; Pearson, A. J. J. Chem. Soc., Chem. Commun. 1976, 601.
34. For other metal-mediated stoichiometric syntheses of 2-cyclohexeneones, see, for instance: (a) Mortimer, M. D.; Carter, J. D.; McElwee-White, L. Organometallics 1993, 12, 4493. (b) McDaniel, K. F.; Kracker, L. R., II; Thamburaj, P. K. Tetrahedron Lett. 1990, 31, 2373. (c) Potter, G. A.; McCague, R. J. J. Chem. Soc., Chem. Commun 1990, 1172. (d) Muzart, J.; Pale, P.; Pete, J.-P. J. Chem. Soc., Chem. Commun. 1981, 668. (e) Birch, A. J.; Pearson, A. J. J. Chem. Soc., Chem. Commun. 1976, 601.
35. For relevent syntheses in terms of bond disconnections of substituted 2-cyclohexenones, see for instance: (a) Yamada, S.-I.; Otani, G. Tetrahedron Lett. 1969, 4237. (b) Ito, Y.; Sawamura, M.; Kominami, K.; Saegusa, T. Tetrahedron Lett. 1985, 26, 5303.-
36. For relevent syntheses in terms of bond disconnections of substituted 2-cyclohexenones, see for instance: (a) Yamada, S.-I.; Otani, G. Tetrahedron Lett. 1969, 4237. (b) Ito, Y.; Sawamura, M.; Kominami, K.; Saegusa, T. Tetrahedron Lett. 1985, 26, 5303.-