Mechanistic studies of the phosphine-catalyzed homodimerization of ketoketenes

Tetrahedron Letters

Volumn 51, Issue 51, 2010, Pages 6690-6694

  Wei, Pei Hsun ^a   Ibrahim, Ahmad A ^a   Mondal, Mukulesh ^a   Nalla, Divya ^a   Harzmann, Gero D ^a   Tedeschi, Frank A ^a   Wheeler, Kraig A ^b   Kerrigan, Nessan J ^a  

^a OAKLAND UNIVERSITY   (United States)

^b EASTERN ILLINOIS UNIVERSITY   (United States)

Author keywords

Lactones; Diastereoselectivity; Disubstituted ketenes; Enolates; Ketenes; Ketoketene dimers; Ketoketenes; Phosphines; Phosphonium enolate

Indexed keywords

4 CHLOROBENZALDEHYDE; ALDEHYDE DERIVATIVE; CHLOROTRIMETHYLSILANE; DIMETHYLKETENE; KETENE DERIVATIVE; KETOKETENE DERIVATIVE; METHYLPHENYLKETENE; PHOSPHINE; PHOSPHONIUM DERIVATIVE; PHOSPHORANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIMERIZATION; NUCLEAR MAGNETIC RESONANCE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 78649316882     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.026     Document Type: Article

References (35)

1. T.T. Tidwell Ketenes 2nd ed. 2006 Wiley New York
2. J.C. Sauer J. Am. Chem. Soc. 69 1947 2444 2448
3. R.H. Hasek, R.D. Clark, E.U. Elam, and J.C. Martin J. Org. Chem. 27 1962 60 64
4. E.U. Elam J. Org. Chem. 32 1967 215 216
5. W.G. Bentrude, and W.D. Johnson J. Am. Chem. Soc. 90 1968 5924 5926
6. W.G. Bentrude, W.D. Johnson, and W.A. Khan J. Am. Chem. Soc. 94 1972 3058 3067
7. Y.E. Aronov, Y.A. Cheburkov, and I.L. Knunyants Izv. Akad. Nauk SSSR, Ser. Khim. 8 1967 1758 1768
8. H.W. Moore, and W.G. Duncan J. Org. Chem. 38 1973 156 158
9. M.A. Calter J. Org. Chem. 61 1996 8006 8007
10. M.A. Calter, and R.K. Orr Org. Lett. 5 2003 4745 4748
11. V.C. Purohit, R.D. Richardson, J.W. Smith, and D. Romo J. Org. Chem. 71 2006 4549 4558
12. M.A. Calter, and X. Guo J. Org. Chem. 63 1998 5308 5309
13. M.A. Calter, W. Song, and J. Zhou J. Org. Chem. 69 2004 1270 1275
14. M.A. Calter, and W. Liao J. Am. Chem. Soc. 124 2002 13127 13129
15. G. Ma, H. Nguyen, and D. Romo Org. Lett. 9 2007 2143 2146
16. Kerrigan, N. J.; Ibrahim, A. A.; Harzmann, G. D. Abstracts of Papers, 236th National Meeting of the American Chemical Society, Philadelphia, PA; American Chemical Society: Washington, DC, 2008; ORGN 531
17. A.A. Ibrahim, G.D. Harzmann, and N.J. Kerrigan J. Org. Chem. 74 2009 1777 1780
18. A.A. Ibrahim, S.M. Smith, S. Henson, and N.J. Kerrigan Tetrahedron Lett. 50 2009 6919 6922
19. H. Lv, Y.-R. Zhang, X.-L. Huang, and S. Ye Adv. Synth. Catal. 350 2008 2715 2718
20. L.M. Baigrie, H.R. Seiklay, and T.T. Tidwell J. Am. Chem. Soc. 107 1985 5391 5396
21. A. Dondoni, G. Fantin, M. Fogagnolo, A. Mastellari, A. Medici, and P. Pedrini J. Org. Chem. 49 1984 3478 3483
22. X.-F. Zhu, C.E. Henry, and O. Kwon J. Am. Chem. Soc. 129 2007 6722 6723
23. 31P NMR Data of Four Coordinate Phosphonium Salts and Betaines J.C. Tebby, Handbook of Phosphorus-31 Nuclear Magnetic Resonance Data 1991 CRC Press Boca Raton, FL 181 226
24. L.W. Dennis, V.J. Bartuska, and G.E. Maciel J. Am. Chem. Soc. 104 1982 230 235
25. D.B. Chestnut, and L.D. Quin Tetrahedron 61 2005 12343 12349
26. E. Vedejs, and S.T. Diver J. Am. Chem. Soc. 115 1993 3358 3359 and references cited therein
27. R.-H. Fan, and X.-L. Hou Tetrahedron Lett. 44 2003 4411 4413
28. 2): δ 13.5.
29. 2P: 543.3386 (m/z). Found: 543.3387.
30. J.E. Baldwin, and J.C. Swallow J. Org. Chem. 35 1970 3583 3584
31. 31P species).
32. 31P species).
33. Spectroscopic data for 11d agreed with that previously reported in: M. Mondal, A.A. Ibrahim, K.A. Wheeler, and N.J. Kerrigan Org. Lett. 12 2010 1664 1667
34. B.L. Hodous, and G.C. Fu J. Am. Chem. Soc. 124 2002 1578 1579
35. A preliminary kinetics investigation has shown that the reaction rate is dependent upon catalyst concentration.