Preparation, characterization, and reactivity of (3-methylpentadienyl) iron(1+) cations

Organometallics

Volumn 26, Issue 22, 2007, Pages 5295-5303

  Chaudhury, Subhabrata ^a   Li, Shukun ^a   Bennett, Dennis W ^b   Siddiquee, Tasneem ^b   Haworth, Daniel T ^a   Donaldson, William A ^a  

^a Marquette University   (United States)

^b UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXENONES; MALONATE; METHYLPENTADIENYL;

CARBON MONOXIDE; NUCLEOPHILES; REACTION KINETICS; REDUCTION; SINGLE CRYSTALS; X RAY ANALYSIS;

IRON COMPOUNDS;

EID: 35748967852     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om7006248     Document Type: Article

References (47)

1. Williams, P. J.; Strauss, C. R.; Wilson, B.; Massy-Westropp, K. A. J. Agrie. Food Chem. 1982, 30, 1219-1223.
2. Kuniyoshi, M.; Marma, M. S.; Higa, T.; Bernardinelli, G.; Jefford, C. W. J. Nat. Prod. 2001, 64, 696-700.
3. (a) Coll, J. C.; Mitchell, S. J.; Stokie, G. J. Tetrahedron Lett. 1977, 1539-1542.
4. (b) Grace, K. J. S.; Zavortink, D.; Jacobs, R. S. Biochem. Pharmacol. 1994, 47, 1427-1434.
5. Bohlmann, F.; Zdero, C. Chem. Ber. 1974, 107, 1416-1419.
6. Muhammad, I.; Mossa, J. S.; Al-Yahya, M. A.; Ramadan, A. F.; El-Feraly, F. S. Photother. Res. 1995, 9, 584-588.
7. Kanokmedhakul, S.; Kanokmedhakul, K.; Kanarsa, T.; Buayairaksa, M. J. Nat. Prod. 2005, 68, 183-188.
8. Hunter, M. S.; Corley, D. G.; Carron, C. P.; Rowold, E.; Kilpatrick, B. F.; Durley, R. C. J. Nat. Prod. 1997, 60, 894-899.
9. There are only two syntheses reported of crotomachlin, a 3-methyll,3(/E)-pentadienyl-containing labdane diterpene: (a) Harlem, D.; Khuong-Huu, F.; Kende, A. S. Tetrahedron Lett. 1993, 34, 5587.
10. (b) Teramoto, T.; Yono, T.; Morita, H.; Katsumura, S.; Sakaguchi, K.; Isoe, S. Synlett 1996, 141.
11. Adams, C. M.; Cerioni, G.; Hafner, A.; Kalchhauser, H.; von Philipsborn, W.; Prewo, R.; Schwenk, A. Helv. Chim. Acta 1988, 71, 1116-1142.
12. (a) Pearson, A. J.; Kole, S. L.; Ray, T. J. Am. Chem. Soc. 1984, 106, 6060-6074.
13. (b) McDaniel, K. F.; Kracker, L. R.; Thamburaj, P. K. Tetrahedron Lett. 1990, 31, 2373-2376.
14. (c) Millot, N.; Guillou, C.; Thai, C. Tetrahedron Lett. 1998, 39, 2325-2326.
15. (d) Barmann, H.; Prahlad, V.; Tao, C.; Yun, Y. K.; Wang, Z.; Donaldson, W. A. Tetrahedron 2000, 56, 2283-2295.
16. Whitesides, T. H.; Budnik, R. A. Inorg. Chem. 1975, 14, 664-676.
17. Wallock, N. J.; Donaldson, W. A. J. Org. Chem. 2004, 9, 2997-3007.
18. (a) Rheingold, A. L.; Haggerty, B. S.; Ma, H.; Ernst, R. D. Acta Cryst. 1996, C52, 1110-1112.
19. (b) Hudson, R. D. A.; Anson, C. E.; Mahon, M. F.; Stephenson, G. R. J. Organomet. Chem. 2001, 630, 88-103.
20. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335-422.
21. Preliminary communication: Chaudhury, S.; Donaldson, W. A. J. Am. Chem. Soc. 2006, 128, 5984-5985.
22. Adams, C. M.; Cerioni, G.; Hafner, A.; Kalchhauser, H.; von Philipsborn, W.; Prewo, R.; Schwenk, A. Helv. Chim. Acta 1988, 71, 1116-1142.
23. (a) Guy, J. J.; Reichert, B. E.; Sheldrick, G. M. Acta Crystallogr., Sect. B 1976, B32, 2504-2506.
24. (b) Donaldson, W. A.; Shang, L.; Rogers, R. D. Organometallics 1994, 13, 6-7.
25. (c) Donaldson, W. A.; Shang, L.; Ramaswamy, M.; Droste, C. A.; Tao, C.; Bennett, D. W. Organometallics 1995, 74, 5119-5126.
26. Sorensen, T. S.; Jablonski, C. R. J. Organomet. Chem. 1970, 25, C62-C66.
27. Nucleophilicity parameters (N, s) for neutral nucleophiles have been assigned from correlation analysis: (a) Mayr, H.; Patz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 938-957.
28. (b) Mayr, H.; Bug, T.; Gotta, M. F.; Hering, N.; Irrgang, B.; Janker, B.; Kempf, B.; Loos, R.; Ofial, A. R.; Remennikov, G.; Schimmel, H. J. Am. Chem. Soc. 2001, 123, 9500-9512.
29. Hossain, M. A.; Jin, M.-J.; Donaldson, W. A. J. Organomet. Chem. 2001, 630, 5-10 and references therein.
30. Carbonyl insertion into (pentenediyl)iron complexes and reductive elimination have previously been reported: (a) Aumann, R. J. Am. Chem. Soc. 1974, 96, 2631-2632.
31. (b) Schulze, M. M.; Gockel, U. J. Organomet. Chem. 1996, 525, 155-158.
32. (c) Taber, D. F.; Kanai, K.; Jiang, Q.; Bui, G. J. Am. Chem. Soc. 2000, 122, 6807-6808.
33. A similar mechanism has been proposed to account for the formation of cyclohexenones from nucleophilic attack of organolithiums on (pentadienyl)iron(l+) cations: McDaniel, K. F.; Kracker, L. R., II; Thamburaj, P. K. Tetrahedron Lett. 1990, 31, 2373-2376.
34. (a) Dobosh, P. A.; Gresham, D. G.; Lillya, C. P.; Magyar, E. S. Inorg. Chem. 1978, 17, 1775-1781.
35. (b) Birch, A. J.; Westerman, P. W.; Pearson, A. J. Aust. J. Chem. 1976, 29, 1671-1677.
36. (a) Clack, D. W.; Monshi, M.; Kane-Maguire, L. A. P. J. Organomet. Chem. 1976, 107, C40-C42.
37. (b) Hoffmann, R.; Hofmann, P. J. J. Am. Chem. Soc. 1976, 98, 598-604.
38. (c) Pfletschinger, A.; Schmalz, H.-G.; Koch, W. Eur-. J. Inorg. Chem. 1999, 1869-1880.
39. (a) Eisenstein, O.; Butler, W. M.; Pearson, A. J. Organometallics 1984, 3, 1150-1157.
40. (b) Pearson, A. J.; Burello, M. P. Organometallics 1992, 11, 448-456.
41. (a) Howell, J. A. S.; Thomas, M. J. J. Chem Soc., Dalton Trans. 1983, 1401-1409.
42. (b) Pearson, A. J.; Blystone, S. L.; Nar, H.; Pinkerton, A. A.; Roden, B. A.; Yoon, J. J. Am. Chem. Soc. 1989, 111, 134-144.
43. + cation.
44. Quinkert, G.; Schwartz, U.; Stark, H.; Weber, W. D.; Adam, F.; Baier, H.; Frank, G.; Duerner, G. Liebigs Ann. Chem. 1982, 1999-2040.
45. 3 complexes) was previously reported: Pearson, A. J.; Gontcharov, A. V. J. Org. Chem. 1998, 63, 152-162.
46. Bennett, D. W.; Siddiquee, T. A.; Haworth, D. T.; Chaudhury, S.; Donaldson, W. A. J. Chem. Crystallogr. 2006, 36, 777-780.
47. Clive, D. L. J.; Murthy, K. S. K.; Wee, A. G. H.; Prasad, J. S.; da Silva, G. V. J.; Majewski, M.; Anderson, P. C.; Evans, C. F.; Haugen, R. D.; Heerze, L. D.; Barrie, J. R. J. Am. Chem. Soc. 1990, 112, 3018-3028.