Additions of acetonitrile and chloroform to aromatic aldehydes in the presence of tetrabutylammonium fluoride

Bulletin of the Korean Chemical Society

Volumn 27, Issue 3, 2006, Pages 432-434

  Eun, Young Ko ^a   Choong, Hwan Lim ^a   Chung, Kyoo Hyun ^a  

^a Inha University   (South Korea)

Author keywords

Cyanomethylation; Nitrile aldol; Oxidation; TBAF; Trichloromethylation

Indexed keywords

EID: 33645224813     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2006.27.3.432     Document Type: Article

References (28)

1. (a) Fleming, F. F.; Shook, B. C. J. Org. Chem. 2002, 67, 3668.
2. (b) Crouse, D. N.; Seebach, D. Chem. Ber. 1968, 101, 3113.
3. Dibiase, S. A.; Lipisko, B. A.; Haag, A.; Wolak, R. A.; Gokel, G. W. J. Org. Chem. 1979, 44, 4640.
4. (a) Vasil'eva, T. T.; Kuz'mina, N. A.; Chakhovskaya, O. V.; Mysova, N. E.; Terent'ev, A. B. Russian J. Org. Chem. 2004, 40, 174.
5. (b) Suto, Y.; Kumagai, N.; Matsunaga, S.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 3147.
6. (c) Caracoti, A.; Flowers II, R. A. Tetrahedron Lett. 2000, 41, 3039.
7. (d) Kisanga, P.; McLeod, D.; D'Sa, B.; Verkade, J. J. Org. Chem. 1999, 64, 3090.
8. (e) Xiao, Z.; Timberlake, J. W. Tetrahedron 1998, 54, 4211.
9. (f) Huang, Y.-Z.; Liao, Y. J. Org. Chem. 1991, 56, 1381.
10. (a) Aggarwal, V. K.; Mereu, A. J. Org. Chem. 2000, 65, 7211.
11. (b) Chen, T. C.; Sumerford, W. T. J. Am. Chem. Soc. 1950, 72, 5124.
12. (c) Reeve, W. Synthesis 1971, 131.
13. (a) Wyvratt, J. M.; Hazen, G. G.; Weinstock, L. M. J. Org. Chem. 1987, 52, 944.
14. (b) Merz, A.; Tomahogh, R. Chem. Ber. 1977, 110, 96.
15. (c) Viehi, H. G.; Franchimont, E.; Valange, P. Chem. Ber. 1963, 96, 426.
16. (d) Bergmann, E. D.; Ginsburg, D. J. Am. Chem. Soc. 1950, 72, 5012.
17. (e) Shono, T.; Kise, N.; Masuda, M.; Suzumoto, T. J. Org. Chem. 1985, 50, 2527.
18. (f) Hideo, T.; Shiro, Y.; Motoi, Y.; Sigeru, T. J. Org. Chem. 1989, 54, 444.
19. Kirmse, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; pp 129-141.
20. (a) Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
21. (b) Krawczyk, S. H.; Townsend, L. B. Tetrahedron Lett. 1991, 32, 5693.
22. Dhar, R. K.; Clawson, D. K.; Fronczek, F. R.; Rabideau, P. W. J. Org. Chem. 1992, 57, 2917.
23. Pless, J. J. Org. Chem. 1974, 39, 2644.
24. (a) Haoran, S.; Stephen, G. D. J. Am. Chem. Soc. 2005, 127, 2050.
25. (b) Chu, C.-K.; Kim, J.-H.; Kim, D. W.; Chung, K.-H.; Katzenellenbogen, J. A.; Chi, D. Y. Bull. Korean Chem. Soc. 2005, 26, 599.
26. A paper on the oxidation will be in submission.
27. Mirta, M. Tetrahedron Lett. 2003, 44, 5823.
28. Corey, E. J.; Link, J. O. Tetrahedron Lett. 1992, 33, 3431.