Ortho-directed lithiation of ω-phenoxy alcohols

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5589-5592

  Salteris, Constantinos S ^a   Kostas, Ioannis D ^a   Micha Screttas, Maria ^a   Heropoulos, George A ^a   Screttas, Constantinos G ^a   Terzis, Aris ^b  

^a INSTITUTE OF BIOLOGY   (Greece)

^b INSTITUTE OF MATERIALS SCIENCE   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BENZALDEHYDE; BENZOPHENONE; CARBON DIOXIDE; CYCLOHEXANE DERIVATIVE; FORMIC ACID; LITHIUM DERIVATIVE; N,N DIMETHYLFORMAMIDE; TETRAHYDROFURAN;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033597844     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990443p     Document Type: Article

References (39)

1. Selected reviews: (a) Klumpp, G. W. Recl. Trav. Chim. Pays-Bas 1986, 105, 1. (b) Snieckus, V. Chem. Rev. 1990, 90, 879.
2. Selected reviews: (a) Klumpp, G. W. Recl. Trav. Chim. Pays- Bas 1986, 105, 1. (b) Snieckus, V. Chem. Rev. 1990, 90, 879.
3. (a) Coitiño, E. L.; Ciuffarin, E.; Floris, F. M.; Tomasi, J. J. Phys. Chem. A 1998, 102, 8369.
4. (b) Rennels, R. A.; Maliakal, A. J.; Collum, D. B. J. Am. Chem. Soc. 1998, 120, 421.
5. (c) Stratakis, M. J. Org. Chem. 1997, 62, 3024.
6. (d) Faigl, F.; Fogassy, K.; Thurner, A.; Tóke, L. Tetrahedron 1997, 53, 4883.
7. (e) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552.
8. (f) Saá, J. M.; Martorell, G.; Frontera, A. J. Org. Chem. 1996, 61, 5194.
9. (g) Beak, P.; Kerrick, S. T.; Gallagher, D. J. J. Am. Chem. Soc. 1993, 115, 10628.
10. (h) Collum, D. B. Acc. Chem. Res. 1992, 25, 448.
11. (a) Mortier, J.; Moyroud, J. J. Org. Chem. 1994, 59, 4042 and references therein.
12. (b) Moyroud, J.; Guesnet, J.-L.; Bennetau, B.; Mortier, J. Bull. Soc. Chim. Fr. 1996, 133, 133.
13. (a) Kostas, I. D.; Screttas, C. G.; Raptopoulou, C. P.; Terzis, A. Tetrahedron Lett. 1997, 38, 8761.
14. (b) Andrieu, J.; Steele, B. R.; Screttas, C. G.; Cardin, C. J.; Fornies, J. Organometallics 1998, 17, 839.
15. Longuet-Higgins, H. C. Quart. Rev. 1957, 11, 121.
16. Screttas, C. G.; Eastham, J. F. J. Am. Chem. Soc. 1965, 87, 3276.
17. (a) Meyer, N.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1978, 17, 521.
18. (b) Meyer, N.; Seebach, D. Chem. Ber. 1980, 113, 1304.
19. Screttas, C. G.; Micha-Screttas, M. Organometallics 1984, 3, 904.
20. (b) Screttas, C. G.; Micha-Screttas, M. J. Organomet. Chem. 1985, 290, 1.
21. (c) Screttas, C. G.; Micha-Screttas, M. J. Organomet. Chem. 1986, 376, 1.
22. (a) Slocum, D. W.; Jennings, C. A. J. Org. Chem. 1976, 41, 3653.
23. (b) Winkle, M. R.; Ronald. R. C. J. Org. Chem. 1982, 47, 2101.
24. (c) Wada, A.; Kanatomo, S.; Nagai, S. Chem. Pharm. Bull. 1985, 33, 1016.
25. One of the reviewers suggested that possibly a bis chelation of the n-BuLi by the substrate is occurring, leading to a less active complex in the solvent system utilized.
26. Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356.
27. Jones, P. R.; Malmberg, C. E.; McGrattan, C. J. Pharm. Sci. 1975, 64, 1240.
28. Almog, J.; Baldwin, J. E.; Crossley, M. J.; Debernardis, J. F.; Dyer, R. L.; Huff, J. R.; Peters, M. K. Tetrahedron 1981, 37, 3589.
29. Review: Bader, A.; Lindner, E. Coord. Chem. Rev. 1991, 108, 27.
30. Liptak, D.; Ilsley, W. H.; Glick, M. D.; Oliver, J. P. J. Organomet. Chem. 1980, 191, 339.
31. Barner, R.; Schmid, H. Helv. Chim. Acta 1960, 43, 1393.
32. Similarly, the attempted conversion of tetramethylene chlorohydrin into ethyl hydroxybutyl ether resulted in cyclization to tetrahydrofuran: Frearson, P. M.; Stern, E. S. J. Chem. Soc. 1958, 3062.
33. +, 10).
34. Diekman, J.; Thomson, J. B.; Djerassi, C. J. Org. Chem. 1968, 33, 2271.
35. Dobrowolska, E.; Eckstein, Z. Przemysl Chem. 1963, 42, 556; Chem. Abstr. 1964, 60, 1637e-f.
36. Dobrowolska, E.; Eckstein, Z. Przemysl Chem. 1963, 42, 556; Chem. Abstr. 1964, 60, 1637e-f.
37. David, S.; Thieffry, A. J. Org. Chem. 1983, 48, 441.
38. Dorn, H. In Preparative Organic Chemistry, 4th ed.; Hilgetag, G., Martini, A., Eds.; John Wiley & Sons: New York, 1972; p 218.
39. Jones, P. R.; Rothenberger, S. D. J. Org. Chem. 1986, 51, 3016.