Regioselective acylation of (5-alkylidene-1,3-cyclohexadiene)tricarbonyliron complexes by the reaction with organometallic reagents

Chemistry Letters

Volumn , Issue 5, 1998, Pages 395-396

  Iwakoshi, Mitsuhiko ^a   Ban, Soo Ho ^a   Hayashi, Yujiro ^a   Narasaka, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001930217     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.395     Document Type: Article

References (16)

1. S. H. Ban, H. Sakurai, Y. Hayashi, and K. Narasaka, Chem. Lett., 1997, 699.
2. S. H. Ban, Y. Hayashi, and K. Narasaka, preceding paper in this issue.
3. a) G. M. Williams and D. E. Rudisill, J. Am. Chem. Soc., 107, 3357 (1985);
4. b) G. M. Williams, R. A. Fisher, and R. H. Heyn, Organometallics, 5, 818 (1986).
5. A. V. Malkov and G. R. Stephenson, J. Organomet. Chem., 489, C44 (1995); A. J. Pearson and K. Srinivasan, J. Org. Chem., 57, 3965 (1992).
6. A. V. Malkov and G. R. Stephenson, J. Organomet. Chem., 489, C44 (1995); A. J. Pearson and K. Srinivasan, J. Org. Chem., 57, 3965 (1992).
7. A. Salzer, H. Schmalle, R. Stauber and S. Streiff, J. Organomet. Chem., 408, 403 (1991); R. J. H. Cowles, B. F. G. Johnson, J. Lewis, and A. W. Parkins, J. Chem. Soc., Dalton Trans., 1972, 1768.
8. A. Salzer, H. Schmalle, R. Stauber and S. Streiff, J. Organomet. Chem., 408, 403 (1991); R. J. H. Cowles, B. F. G. Johnson, J. Lewis, and A. W. Parkins, J. Chem. Soc., Dalton Trans., 1972, 1768.
9. -1.
10. 13C-resonance of the acetyl carbon of acetyldicarbonylcyclopentadienyliron is reported to be 254.4 ppm. L. F. Farnell, E. W. Randall, and E. Rosenberg, J. Chem. Soc., Chem. Commun., 1971, 1078.
11. -1.
12. Other oxidation methods, such as cerium(IV) ammonium nitrate (CAN) in MeOH and iodine in THF gave 9a in lower yield.
13. 3NO was added. The reaction mixture was stirred for 12 h. 9b was obtained after the purification by TLC (48.1 mg, 0.22 mmol, 72% from 5 (83.3 mg, 0.30 mmol)).
14. Organolithium reagent reacts with ethoxycarbonyl group of 12.
15. M. F. Semmelhack and J. W. Herndon, Organomettallics, 2, 363 (1983).
16. H. Heaney, "The Bimolecular Aromatic Friedel-Crafts Reaction," in "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 2, p 733.