Reaction of the 2-(bromodifluoromethyl)benzoxazole with tetrakis(dimethylamino)ethylene (TDAE) in the presence of aldehydes. A convenient synthesis of 2-(difluoromethyl)benzoxazole alcohols.

Tetrahedron Letters

Volumn 38, Issue 5, 1997, Pages 821-824

  Burkholder, Conrad ^a   Dolbier Jr , William R ^a   Médebielle, Maurice ^b  

^a UNIVERSITY OF FLORIDA   (United States)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOXAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ELECTROCHEMISTRY; METHODOLOGY; REACTION ANALYSIS;

EID: 0031018726     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02440-9     Document Type: Article

References (18)

1. Tozer, M. J.: Herpin, T. Tetrahedron. 1996, 52, 8619-8683.
2. Welch, J. T.; Eswarakrishnan, S. 'Fluorine in Bioorganic Chemistry', John Wiley & Sons, Inc., New York, 1991.
3. (a). Médebielle, M. Tetrahedron. Lett. 1996, 37, 5119-5122.
4. (b). Médebielle, M. Tetrahedron. Lett. 1995, 36, 2071-2074.
5. (c). Qiu, Z-M.; Burton, D. J. J. Org. Chem. 1995, 60, 5570.
6. (d). Itoh, T.; Ohara, H.; Emoto, S. Tetrahedron. Lett. 1995, 36, 3531-3534.
7. (e). Buttle, L. A.; Mothcrwell, W. B Tetrahedron. Lett. 1994, 35, 3995-3998.
8. Patel, S. T.; Percy, J. M.: Wilkes, R. D. J. Org. Chem. 1996, 61, 166-173 and references cited therein.
9. Wiberg, N. Angew. Chem. 1968, 20, 809-856.
10. (a) This observation is comparable to values of -0.53 and -0.68V: Fox, J. R.; Foxman, B. M.; Guarrera, D.; Miller, J. S.: Calabrese, J. C.; Reis, Jr., A. H. J. Mater. Chem. 1996, 6, 1627-1631.
11. (b). This observation is comparable to value of -0.57V: Bock, H.; Jaculi, D. Angew. Chem.. Int. Ed. Engl. 1984, 23, 305.
12. (a) Pawelke, G. J. Fluorine. Chem. 1989, 42, 429-433.
13. (b) Pawelke, G. J. Fluorine. Chem. 1991, 52, 229-234.
14. (a) Briscoe, M. W.; Chambers, R. D.; Mullins, S. J.: Nakamura, T.; Vaughan, J. F. S.; Drakesmith, F. G. J. Chem. Soc. Perkin. Trans. 1, 1994, 3115-3118.
15. (b) Chambers, R. D.; Vaughan, J. F. S.; Mullins, S. J.; Nakamura, T.; Roche, A. J. J. Fluorine. Chem. 1995, 72, 231-233.
16. (c). Chambers, R. D.; Gray, W. K.; Korn, S. T. Tetrahedron. 1995, 51, 13167-13176.
17. Burkholder, C.; Dolbier, Jr., W. R.; Médebielle, M. submitted.
18. +). Analysis: Calcd. C 60.87, H 3.62, N 10.14. Found C 61.02, H 3.83, N 10.18.